[4-(2-Nitro-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester → Methyl 2-{4-[2-amino-4-(trifluoromethyl)phenoxy]-phenyl}acetate

HRID 2252270Notes

Reaction equation

HRID 2252270 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[N+:22]([O-])=O)=[CH:7][CH:6]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][C:13]=2[NH2:22])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 9112380[4-(2-Nitro-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester

Product 1

HCID 26189410Methyl 2-{4-[2-amino-4-(trifluoromethyl)phenoxy]-phenyl}acetateYield 79.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [4-(2-nitro-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester (1.31 g, 3.54 mmol) and 10% Pd/C (377 mg, 0.354 mmol) in 17 mL of methanol was allowed to stir at room temperature under hydrogen atmosphere for 12 h. Upon completion, the mixture was filtered through a short column of celite and the filtrate was concentrated in vacuo to give 920 mg of [4-(2-Amino-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester. 1H NMR (CDCl3): δ 7.24-7.33 (m, 3H), 6.80-7.06 (m, 4H), 4.01 (br s, 2H), 3.71 (s, 3H), 3.61 (s, 2H). LCMS (ESI+) 326 (M+1).

Workup

  1. filtrationUpon completion, the mixture was filtered through a short column of celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fa85dc5327c14400b5f6a9233c450e67
Source dataset
uspto-grants-2008_01
Patent number
US07321001B2

Reaction notes

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