Ethyl 2-fluoro-4-nitrobenzoate → Ethyl 4-Amino-2-fluorobenzoate

HRID 53289Notes

Reaction equation

HRID 53289 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[F:14])[CH3:2]>CO.[Pt](=O)=O>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[F:14])[CH3:2]

Participants

4

Reactant 1

HCID 10727300Ethyl 2-fluoro-4-nitrobenzoate

Product 1

HCID 10797532Ethyl 4-Amino-2-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-fluoro-4-nitrobenzoic acid ethyl ester (770 mg, 3.62 mmol) in methyl alcohol (15 mL) was treated with platinum (IV) oxide (75 mg) at 40 psi of H2. After 0.5 h the reaction mixture was filtered through celite and concentrated in vacuo to give 700 mg (Y: 99%) of the title product; 1H-NMR (CDCl3): δ7.76 (t, J=8.3 Hz, 1H), 6.42 (d, J=8.5 Hz, 1H), 6.35 (d, J=12.9 Hz, 1H), 4.33 (q, J=7.1 Hz, 2H), 4.20 (bs, 2H), 1.36 (t, J=7.1 Hz, 3H); MS (DCI) m/e: 184 (MH+).

Workup

  1. filtrationAfter 0.5 h the reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9744a531e7a0497c8918385974afccaf
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Reaction notes

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