Dimethyl 2-(2-fluoro-4-nitrophenyl)malonate → Dimethyl 2-(4-amino-2-fluorophenyl)malonate

HRID 1842959Notes

Reaction equation

HRID 1842959 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH:11]([C:16]([O:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13]>C(O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH:11]([C:12]([O:14][CH3:15])=[O:13])[C:16]([O:18][CH3:19])=[O:17])=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 1

HCID 53429620Dimethyl 2-(2-fluoro-4-nitrophenyl)malonate

Product 1

HCID 86672160Dimethyl 2-(4-amino-2-fluorophenyl)malonateYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred ethanol solution (40 mL) of dimethyl 2-(2-fluoro-4-nitrophenyl)malonate (4.0 g, 14.76 mmol, 1.0 eq) 10% Pd—C (400 mg) was added and the mixture was stirred under a H2 gas balloon at RT for 2 h, then the mixture was passed through a celite bed and the solvent of the filtrate was evaporated to get dimethyl 2-(4-amino-2-fluorophenyl)malonate (3.2 g, 87%, solid; TLC system: EtOAc/PE (3:7), Rf: 0.3).

Workup

  1. customthe solvent of the filtrate was evaporated

Sources & evidence

ORD record
ord-ac19f87d1f194fceaed79aa50ed3de9f
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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