HCID 59164426, compound → HCID 59164448, compound

HRID 1894119Notes

Reaction equation

HRID 1894119 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([F:12])[CH3:11])=[CH:6][C:5]=1[N+:13]([O-])=O>CO.CCO.[Ni]>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([F:12])[CH3:11])=[CH:6][C:5]=1[NH2:13]

Participants

5

Reactant 1

HCID 59164426HCID 59164426, compound

Product 1

HCID 59164448HCID 59164448, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 4-(1-fluoro-ethyl)-2-nitro-benzoic acid methyl ester (0.6 g, 2.64 mmol) in MeOH (15 mL) was treated with Nickel-raney in EtOH (254 mL) and the mixture was stirred at r.t. for 3 h under H2 (0.1 bar). The mixture was then filtered and concentrated in vacuo to give 2-amino-4-(1-fluoro-ethyl)-benzoic acid methyl ester (334 g, 1.69 mmol, 93%) as a yellow oil. ESI-MS: m/z 198 [M+H]+, rt 4.86 min.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1472457b45af444f9faaea08118a5b81
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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