1-Fluoro-2-nitrobenzene → 4-Methyl-2-(2-nitro-phenylamino)-benzonitrile

HRID 131310

반응식

HRID 131310 반응식
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15].O.[OH-].[Li+]>CS(C)=O>[CH3:20][C:18]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([NH:11][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:19]=1

참가 물질

5

반응물 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 28012762-Amino-4-methylbenzonitrile

생성물 1

HCID 210935294-Methyl-2-(2-nitro-phenylamino)-benzonitrile

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Combine 1-fluoro-2-nitro-benzene (5.34 g, 37.83 mmol), 2-amino-4-methyl-benzonitrile (5.00 g, 37.83 mmol), lithium hydroxide monohydrate (3.17 g, 75.66 mmol) and DMSO (70.0 ml) and stir at 55° C. Afer 16 hours; cool to ambient temperature, pour the mixture onto ice chips and stir. After 1 hour, remove the resulting yellow precipitate by vacuum filtration. Dry the precipitate under vacuum, recrystallize in ethanol to give 5.15 g (54%) of fine, amber colored needles: mp 162-164° C.; mass spectrum (ion spray): m/z 254.0 (M+1).

후처리

  1. customAfer 16 hours
  2. additionpour the mixture onto ice chips
  3. customremove the resulting yellow precipitate
  4. filtrationby vacuum filtration
  5. customDry the precipitate under vacuum
  6. customrecrystallize in ethanol
  7. customto give 5.15 g (54%) of fine, amber colored needles

출처 및 근거

ORD 기록
ord-357fcf9ce6314f65ad7576ea9c7b50b7
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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