Ethyl 2-methylacetoacetate → 2-(3-Amino-2-cyano-4-nitrophenyl)-2-methyl-3-oxobutyric acid ethyl ester

HRID 1634226노트

반응식

HRID 1634226 반응식
[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6](Cl)[C:3]=1[C:4]#[N:5].[CH3:14][CH:15]([C:21]([CH3:23])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:18][C:16](=[O:17])[C:15]([C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([NH2:1])[C:3]=1[C:4]#[N:5])([CH3:14])[C:21](=[O:22])[CH3:23])[CH3:20]

참가 물질

6

반응물 3

HCID 701Ethyl 2-methylacetoacetateHCID 11430Potassium CarbonateHCID 112756272-Amino-6-chloro-3-nitro-benzonitrile

생성물 1

HCID 112667142-(3-Amino-2-cyano-4-nitrophenyl)-2-methyl-3-oxobutyric acid ethyl ester수율 46%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-amino-6-chloro-3-nitrobenzonitrile (1.97 g, 10 mmol) and ethyl 2-methylacetoacetate (3.6 g, 25 mmol) in DMF (10 mL) was added finely powdered K2CO3, and the mixture stirred vigorously for 24 h. The deep red mixture was diluted with EtOAc and washed in turn with 2M HCl, water and brine. The residue after evaporation was purified by flash chromatography in hexane/EtOAc 3:1 to yield 2-(3-amino-2-cyano-4-nitrophenyl)-2-methyl-3-oxobutyric acid ethyl ester as an oil (1.39 g, 46%), MS (NH3 CI) 323 (M+NH4+), 293 (M+NH4—NO+).

후처리

  1. washwashed in turn with 2M HCl, water and brine
  2. customThe residue after evaporation
  3. customwas purified by flash chromatography in hexane/EtOAc 3:1

출처 및 근거

ORD 기록
ord-7c40e6e70fae4faeab55fe122ac0ba9f
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06506769B2

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