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 1835096Notes

Reaction equation

HRID 1835096 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

HCID 110661612-(4-Amino-2-cyano-3-methylamino-phenyl)-2-methyl-3-oxo-butyric acid ethyl esterYield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the above ester (10.5 g, 32.5 mmol) in EtOAc (130 mL) was hydrogenated over 10% palladium on carbon (0.5 g) at 50 psi for 24 h. The catalyst was removed by filtration through diatomaceous earth, and the filtrate was evaporated. A mixture of EtOAc/hexane (1:1, 10 mL) was added to the residue and the resulting mixture was stirred for 0.5 h. The crystals were filtered and washed with hexane to give 2-(4-amino-2-cyano-3-methylaminophenyl)-2-methyl-3-oxobutyric acid ethyl ester (7.74 g, 81%), mp 118-123° C.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate was evaporated
  3. additionA mixture of EtOAc/hexane (1:1, 10 mL)
  4. additionwas added to the residue
  5. filtrationThe crystals were filtered
  6. washwashed with hexane

Sources & evidence

ORD record
ord-7478c08548a54cc58812bb3cd13d1375
Source dataset
uspto-grants-2004_08
Patent number
US06770639B2

Reaction notes

Loading…