4-Methyl-2-nitroaniline → 2-Chloro-6-nitro-p-toluidine

HRID 3135

反応式

HRID 3135 の反応式
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Cl:12]Cl>C(Cl)(Cl)Cl>[Cl:12][C:7]1[CH:8]=[C:2]([CH3:1])[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]=1[NH2:6]

参加物

4

反応物 2

HCID 69784-Methyl-2-nitroanilineHCID 24526Chlorine

生成物 1

HCID 795952-Chloro-6-nitro-p-toluidine収率 25%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

To a stirred solution of 4-methyl-2-nitroaniline (19.69 g, 129.4 mM) in chloroform (200 mL) under a nitrogen atmosphere was added dropwise a solution of chlorine (10.15 g, 285.9 mM) in chloroform (100 mL) while maintaining the reaction mixture temperature below 30° C. The reaction mixture was stirred for 3 days and then washed with aqueous sodium bicarbonate. The organic phase was then concentrated and the residue chromatographed (eluant: hexane/diethyl ether; 9/1) over silica gel to provide (6.03 g, 25%) the title compound as an orange crystalline solid, mp 68.5°-69.5° C.; MS(CI): 187 (M+H).

後処理

  1. temperaturewhile maintaining the reaction mixture temperature below 30° C
  2. washwashed with aqueous sodium bicarbonate
  3. concentrationThe organic phase was then concentrated
  4. customthe residue chromatographed (eluant: hexane/diethyl ether; 9/1) over silica gel

出典と根拠

ORDレコード
ord-29cf4cf9cdd54ff580a9152a0791fb0b
出典データセット
uspto-grants-1998_03
特許番号
US05733910

関連ノート

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