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

HRID 1835092ノート

反応式

HRID 1835092 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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 2 M 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+).

後処理

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

出典と根拠

ORDレコード
ord-7c6e14120e10446ab66a4f3de1eb8da1
出典データセット
uspto-grants-2004_08
特許番号
US06770639B2

反応ノート

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