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 |
| 巻 | 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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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
}
TY - JOUR
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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U2 - 10.1246/nikkashi.1979.1532
DO - 10.1246/nikkashi.1979.1532
M3 - Article
AN - SCOPUS:85016528694
VL - 1979
SP - 1532
EP - 1535
JO - Nippon Kagaku Kaishi / Chemical Society of Japan - Chemistry and Industrial Chemistry Journal
JF - Nippon Kagaku Kaishi / Chemical Society of Japan - Chemistry and Industrial Chemistry Journal
SN - 0369-4577
IS - 11
ER -