Catalytic Reduction of o-Nitroanisole with Hydrogen in Sulfuric Acid-Methanol Solution

Takaaki Sone, Masami Karikura, Seiji Shinkai, Osamu Manabe

研究成果: ジャーナルへの寄稿記事

2 引用 (Scopus)

抄録

Catalytic reduction (5% platinum or 5% palladium placed on carbon and under 1 atm of H2) of o-nitroanisole [1 ] with hydrogen was carried out in sulfuric acid-methanol solution at a room temperature. The reaction products were o-anisidine [2], 2,4-dimethoxyaniline [3], and 2,6-dimethoxyaniline [4]. The products [3] and [4] were considered to form in terms of the Bamberger-type rearrangement of o-methoxyphenylhydroxylamine, formed in the course of catalytic reduction of [1] to [2]. The yield of amines ([2], [3], [4]) was significantly dependent upon the amount of sulfuric acid. Pt-C catalyst is more effective than Pd-C to obtain significant amount of [3] and [4]. When catalytic reduction of [1] (4.0g) over Pt-C (120mg) was carried out in 40ml of methanol, the maximum yield of [4] achieved when 20.0 g of sulfuric acid was added (the yield of [2],[3] or [4] being 56%, 12%, or 27%, respectively) and that of [3] was achieved when 40.0g of sulfuric acid was added (the yield of [2], [3], or [4] being 33%, 26% or 2%, respectively). It was also found that addition of dimethyl sulfoxide, a catalyst poison, enhances significantly the yield of rearrangement products: for example, while the yield of [2], [3], or [4] being 81%, 18%, or 1%, respectively, in the case of 2.8 g of sulfuric acid and in the absence of dimethyl sulfoxide, the yeild of [2], [3], or [4] being 55%, 28%, 9%, respectively, in the presence of dimethyl sulfoxide (0.05 ml).

元の言語英語
ページ(範囲)1532-1535
ページ数4
ジャーナルNippon Kagaku Kaishi
1979
発行部数11
DOI
出版物ステータス出版済み - 1979
外部発表Yes

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Sulfuric acid
Methanol
Hydrogen
Dimethyl sulfoxide
Dimethyl Sulfoxide
Catalysts
Poisons
Palladium
Platinum
Reaction products
Amines
Carbon
2-nitroanisole
sulfuric acid
Temperature

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

これを引用

Catalytic Reduction of o-Nitroanisole with Hydrogen in Sulfuric Acid-Methanol Solution. / Sone, Takaaki; Karikura, Masami; Shinkai, Seiji; Manabe, Osamu.

:: Nippon Kagaku Kaishi, 巻 1979, 番号 11, 1979, p. 1532-1535.

研究成果: ジャーナルへの寄稿記事

Sone, Takaaki ; Karikura, Masami ; Shinkai, Seiji ; Manabe, Osamu. / Catalytic Reduction of o-Nitroanisole with Hydrogen in Sulfuric Acid-Methanol Solution. :: Nippon Kagaku Kaishi. 1979 ; 巻 1979, 番号 11. pp. 1532-1535.
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title = "Catalytic Reduction of o-Nitroanisole with Hydrogen in Sulfuric Acid-Methanol Solution",
abstract = "Catalytic reduction (5{\%} platinum or 5{\%} palladium placed on carbon and under 1 atm of H2) of o-nitroanisole [1 ] with hydrogen was carried out in sulfuric acid-methanol solution at a room temperature. The reaction products were o-anisidine [2], 2,4-dimethoxyaniline [3], and 2,6-dimethoxyaniline [4]. The products [3] and [4] were considered to form in terms of the Bamberger-type rearrangement of o-methoxyphenylhydroxylamine, formed in the course of catalytic reduction of [1] to [2]. The yield of amines ([2], [3], [4]) was significantly dependent upon the amount of sulfuric acid. Pt-C catalyst is more effective than Pd-C to obtain significant amount of [3] and [4]. When catalytic reduction of [1] (4.0g) over Pt-C (120mg) was carried out in 40ml of methanol, the maximum yield of [4] achieved when 20.0 g of sulfuric acid was added (the yield of [2],[3] or [4] being 56{\%}, 12{\%}, or 27{\%}, respectively) and that of [3] was achieved when 40.0g of sulfuric acid was added (the yield of [2], [3], or [4] being 33{\%}, 26{\%} or 2{\%}, respectively). It was also found that addition of dimethyl sulfoxide, a catalyst poison, enhances significantly the yield of rearrangement products: for example, while the yield of [2], [3], or [4] being 81{\%}, 18{\%}, or 1{\%}, respectively, in the case of 2.8 g of sulfuric acid and in the absence of dimethyl sulfoxide, the yeild of [2], [3], or [4] being 55{\%}, 28{\%}, 9{\%}, respectively, in the presence of dimethyl sulfoxide (0.05 ml).",
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T1 - Catalytic Reduction of o-Nitroanisole with Hydrogen in Sulfuric Acid-Methanol Solution

AU - Sone, Takaaki

AU - Karikura, Masami

AU - Shinkai, Seiji

AU - Manabe, Osamu

PY - 1979

Y1 - 1979

N2 - Catalytic reduction (5% platinum or 5% palladium placed on carbon and under 1 atm of H2) of o-nitroanisole [1 ] with hydrogen was carried out in sulfuric acid-methanol solution at a room temperature. The reaction products were o-anisidine [2], 2,4-dimethoxyaniline [3], and 2,6-dimethoxyaniline [4]. The products [3] and [4] were considered to form in terms of the Bamberger-type rearrangement of o-methoxyphenylhydroxylamine, formed in the course of catalytic reduction of [1] to [2]. The yield of amines ([2], [3], [4]) was significantly dependent upon the amount of sulfuric acid. Pt-C catalyst is more effective than Pd-C to obtain significant amount of [3] and [4]. When catalytic reduction of [1] (4.0g) over Pt-C (120mg) was carried out in 40ml of methanol, the maximum yield of [4] achieved when 20.0 g of sulfuric acid was added (the yield of [2],[3] or [4] being 56%, 12%, or 27%, respectively) and that of [3] was achieved when 40.0g of sulfuric acid was added (the yield of [2], [3], or [4] being 33%, 26% or 2%, respectively). It was also found that addition of dimethyl sulfoxide, a catalyst poison, enhances significantly the yield of rearrangement products: for example, while the yield of [2], [3], or [4] being 81%, 18%, or 1%, respectively, in the case of 2.8 g of sulfuric acid and in the absence of dimethyl sulfoxide, the yeild of [2], [3], or [4] being 55%, 28%, 9%, respectively, in the presence of dimethyl sulfoxide (0.05 ml).

AB - Catalytic reduction (5% platinum or 5% palladium placed on carbon and under 1 atm of H2) of o-nitroanisole [1 ] with hydrogen was carried out in sulfuric acid-methanol solution at a room temperature. The reaction products were o-anisidine [2], 2,4-dimethoxyaniline [3], and 2,6-dimethoxyaniline [4]. The products [3] and [4] were considered to form in terms of the Bamberger-type rearrangement of o-methoxyphenylhydroxylamine, formed in the course of catalytic reduction of [1] to [2]. The yield of amines ([2], [3], [4]) was significantly dependent upon the amount of sulfuric acid. Pt-C catalyst is more effective than Pd-C to obtain significant amount of [3] and [4]. When catalytic reduction of [1] (4.0g) over Pt-C (120mg) was carried out in 40ml of methanol, the maximum yield of [4] achieved when 20.0 g of sulfuric acid was added (the yield of [2],[3] or [4] being 56%, 12%, or 27%, respectively) and that of [3] was achieved when 40.0g of sulfuric acid was added (the yield of [2], [3], or [4] being 33%, 26% or 2%, respectively). It was also found that addition of dimethyl sulfoxide, a catalyst poison, enhances significantly the yield of rearrangement products: for example, while the yield of [2], [3], or [4] being 81%, 18%, or 1%, respectively, in the case of 2.8 g of sulfuric acid and in the absence of dimethyl sulfoxide, the yeild of [2], [3], or [4] being 55%, 28%, 9%, respectively, in the presence of dimethyl sulfoxide (0.05 ml).

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JO - Nippon Kagaku Kaishi / Chemical Society of Japan - Chemistry and Industrial Chemistry Journal

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