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

HRID 1449583

반응식

HRID 1449583 반응식
[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]

참가 물질

4

반응물 2

HCID 69784-Methyl-2-nitroanilineHCID 24526Chlorine

생성물 1

HCID 795952-Chloro-6-nitro-p-toluidine수율 25%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6e36f81fd66f4fa192caafe891bd1d04
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599814

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