2-Nitro-4-vinyl-benzoic acid methyl ester → Methyl 2-amino-4-ethylbenzoate

HRID 906600Notes

Reaction equation

HRID 906600 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH2:11])=[CH:6][C:5]=1[N+:12]([O-])=O>CO.[Pd]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[CH:6][C:5]=1[NH2:12]

Participants

4

Reactant 1

HCID 591644672-Nitro-4-vinyl-benzoic acid methyl ester

Product 1

HCID 59164409Methyl 2-amino-4-ethylbenzoateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-nitro-4-vinyl-benzoic acid methyl ester (820 mg, 3.96 mmol) in MeOH (15 mL) was shaken under H2 (0.1 bar) in the presence of Pd/C (10%, 0.2 g) at 50° C. for 5 h. After cooling to r.t., the reaction mixture was filtered and the solvent was removed in vacuo to provide the title product (680 mg, 96%) which was used in the next step without further purification. ESI-MS: m/z 180.1 [M+H]+, rt 5.13 min

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-564be098cfa849be98dee7b70f2be1e1
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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