Ethyl 2-(2-chloro-4-fluoro-5-nitrophenyl)acetate → Ethyl 2-(5-amino-2-chloro-4-fluorophenyl)acetate

HRID 1257182Notes

Reaction equation

HRID 1257182 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>CCO.[Ni]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Cl:1])=[C:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1

Participants

4

Reactant 1

HCID 68984950Ethyl 2-(2-chloro-4-fluoro-5-nitrophenyl)acetate

Product 1

HCID 69297881Ethyl 2-(5-amino-2-chloro-4-fluorophenyl)acetateYield 95.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(2-chloro-4-fluoro-5-nitrophenyl)acetate (22.5 g, 86.2 mmol) in EtOH (200 mL) was stirred with Raney Ni (20% slurry in water, 5.0 g, 17 mmol) under a hydrogen atmosphere (30 psi) for 5 h. The catalyst was removed by filtration and the filtrate was concentrated to give ethyl 2-(5-amino-2-chloro-4-fluorophenyl)acetate (19 g, 95% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.10 (d, J=11.2 Hz, 1H), 6.71 (d, J=9.2 Hz, 1H), 5.27 (s, 2H), 4.05 (q, J=6.8 Hz, 2H), 3.57 (s, 2H), 1.14 (t, J=6.8 Hz, 3H); MS (ESI) m/z: 232.0 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-bfde4753e88f4ab980d9775d9a337a07
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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