Ethyl 2-cyano-4-fluoro-5-nitrophenylacetate → Ethyl 2-(5-amino-2-cyano-4-fluorophenyl)acetate

HRID 1930311Notes

Reaction equation

HRID 1930311 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([F:9])[C:6]([N+:10]([O-])=O)=[CH:5][C:4]=1[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:2]>CO.CCOC(C)=O.[Pd]>[NH2:10][C:6]1[C:7]([F:9])=[CH:8][C:3]([C:1]#[N:2])=[C:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=1

Participants

5

Reactant 1

HCID 69088377Ethyl 2-cyano-4-fluoro-5-nitrophenylacetate

Product 1

HCID 68982767Ethyl 2-(5-amino-2-cyano-4-fluorophenyl)acetateYield 81%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-(2-cyano-4-fluoro-5-nitrophenyl)acetate in methanol and EtOAc (1:1, 10 mL) was added 10% Pd/C. The solution was stirred under H2 (1 arm) at RT for 3 days. The solution was filtered and evaporated to obtain ethyl 2-(5-amino-2-cyano-4-fluorophenyl)acetate (0.21 g, 81% yield).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-23f82806e2494fd091ad75ccf62a394e
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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