2-(2-Cyano-3-methylamino-4-nitrophenyl)-2-methyl-3-oxobutyric acid ethyl ester → 2-(4-Amino-2-cyano-3-methylamino-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester

HRID 562422ノート

反応式

HRID 562422 の反応式
[CH2:1]([O:3][C:4](=[O:23])[C:5]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([NH:19][CH3:20])[C:11]=1[C:21]#[N:22])([CH3:9])[C:6](=[O:8])[CH3:7])[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[C:5]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH:19][CH3:20])[C:11]=1[C:21]#[N:22])([CH3:9])[C:6](=[O:8])[CH3:7])[CH3:2]

参加物

4

反応物 1

HCID 120354712-(2-Cyano-3-methylamino-4-nitrophenyl)-2-methyl-3-oxobutyric acid ethyl ester

生成物 1

HCID 110661612-(4-Amino-2-cyano-3-methylamino-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester収率 107%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a 500 mL Parr pressure flask was added 2-(2-cyano-3-methylamino-4-nitro-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester (7.13 g, 16.5 mmol) as a solution in EtOAc (50 mL) followed by 10% palladium on carbon (1.0 g). The flask was purged under vacuum, then charged with hydrogen gas (50 psi). The flask was agitated at room temperature for while open to the ballast (caution: potential exotherm). After 8 hours, TLC analysis indicated that all starting material has been consumed. The reaction mixture was filtered through a pad of celite and washed with EtOAc. The resulting solution was concentrated to provide 2-(4-amino-2-cyano-3-methylamino-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester (5.11 g, 77%) as a gray solid, which was used without further purification. 1H NMR (400 MHz, d6-DMSO) δ 6.70 (d, J=8.2 Hz, 1H), 6.33 (d, J=8.2 Hz, 1H), 6.17 (s, 2H), 4.90 (q, J1=5.1 Hz, J2=10.6 Hz, 1H), 4.21-4.15 (m, 2H), 2.95 (d, J=5.5 Hz, 2H), 2.22 (s, 3H), 1.66 (s, 3H), 1.2 (t, J=7.0 Hz, 3H).

後処理

  1. customThe flask was purged under vacuum
  2. additioncharged with hydrogen gas (50 psi)
  3. customhas been consumed
  4. filtrationThe reaction mixture was filtered through a pad of celite
  5. washwashed with EtOAc
  6. concentrationThe resulting solution was concentrated

出典と根拠

ORDレコード
ord-73c899da47704f3db4074453d5c03a06
出典データセット
uspto-grants-2011_11
特許番号
US08067395B2

反応ノート

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