3-Chloro-2-methyl-6-nitroaniline → 4-Chloro-3-methylbenzene-1,2-diamine

HRID 1739599ノート

反応式

HRID 1739599 の反応式
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([C:6]([N+:9]([O-])=O)=[CH:7][CH:8]=1)[NH2:5]>Cl>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([NH2:5])[C:6]([NH2:9])=[CH:7][CH:8]=1

参加物

3

反応物 1

HCID 129530203-Chloro-2-methyl-6-nitroaniline

生成物 1

HCID 218358734-Chloro-3-methylbenzene-1,2-diamine

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

The reaction sequence set out in FIG. 4 is as follows: 3-chloro-2-methylacetanilide was prepared from 3-chloro-2-methylaniline via acetylation of the aniline with acetic anhydride in an aqueous methanol solution. A mixture of chloro-methylnitro-acetanilide isomers was thereafter formed by nitration of the acetanilide with sulfuric and nitric acid. The 3-chloro-2-methyl4-nitro isomer was removed by precipitation after addition of potassium hydroxide to the mixture of isomer in ethanol. The 3-chloro-2-methyl-6-nitroacetanilide was heated to reflux in an aqueous sodium hydroxide solution. The solid that formed was 3-chloro-2-methyl-6-nitroaniline. Reaction with a solution of stannous chloride in hydrochloric acid yielded a precipitate of 4-chloro-3-methyl-1,2-benzenediamine. Reaction with sodium nitrite in acetic acid yielded a solid 5-chloro4-methylbenzotriazole.

後処理

  1. customThe 3-chloro-2-methyl4-nitro isomer was removed by precipitation
  2. additionafter addition of potassium hydroxide
  3. additionto the mixture of isomer in ethanol
  4. temperatureThe 3-chloro-2-methyl-6-nitroacetanilide was heated
  5. temperatureto reflux in an aqueous sodium hydroxide solution
  6. customThe solid that formed

出典と根拠

ORDレコード
ord-64d333f6281443a89f3330f54caff650
出典データセット
uspto-grants-1999_10
特許番号
US05968408

反応ノート

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