4-Chloro-2-nitroaniline → Methyl 4-{[(4-chloro-2-nitrophenyl)amino]methyl}benzoate

HRID 1594512

반응식

HRID 1594512 반응식
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[H-].[Na+].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][CH:18]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:23][C:20]2[CH:21]=[CH:22][C:17]([C:16]([O:15][CH3:14])=[O:25])=[CH:18][CH:19]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

참가 물질

6

반응물 4

HCID 69794-Chloro-2-nitroanilineHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 516892Sodium Bicarbonate

생성물 1

HCID 69417003Methyl 4-{[(4-chloro-2-nitrophenyl)amino]methyl}benzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To 4-chloro-2-nitroaniline (10 mmol, 1.73 g) in DMF (10 mL) was added NaH (11 mmol, 440 mg of 60% suspension in mineral oil). After 30 min the reaction vessel was placed in a water bath and methyl-4-(bromomethyl)benzoate (11 mmol, 2.52 g) was added (exothermic). The reaction mixture was allowed to stand at ambient temperature for 16 h, then poured into saturated NaHCO3, affording an orange precipitate which was filtered, washed with water and dried in vacuo. Purification by flash chromatography on silica eluting with 15% EtOAc in hexanes provided the product as an orange solid. LC-MS (ESI, Method C) 3.79 min, m/z 321.1 (M+1).

후처리

  1. waitto stand at ambient temperature for 16 h
  2. customaffording an orange precipitate which
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried in vacuo
  6. customPurification by flash chromatography on silica eluting with 15% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-4eebdbbf94ca42fc812379add2d10d30
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07301036B2

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