2'-Nitro-4'-(trifluoromethyl)-[1,1'-biphenyl]-3-acetic acid ethyl ester → 2'-Amino-4'-(trifluoromethyl)-[1,1'-biphenyl]-3-acetic acid ethyl ester

HRID 1696455Notes

Reaction equation

HRID 1696455 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:7]=[C:8]([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:9]=[CH:10][CH:11]=1)[CH3:2]>C1COCC1.[Ni]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:14][C:13]=2[NH2:22])[CH:9]=[CH:10][CH:11]=1)[CH3:2]

Participants

4

Reactant 1

HCID 672710532'-Nitro-4'-(trifluoromethyl)-[1,1'-biphenyl]-3-acetic acid ethyl ester

Product 1

HCID 672715402'-Amino-4'-(trifluoromethyl)-[1,1'-biphenyl]-3-acetic acid ethyl esterYield 59.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

2′-Nitro-4′-(trifluoromethyl)-[1,1′-biphenyl]-3-acetic acid ethyl ester (107 mg, 0.30 mmol) in THF (6 mL) was treated with about 150 mg of Raney® nickel (50 wt % in H2O). The reaction was shaken on a Parr apparatus under 50 psi of H2. After 4.5 h, another 200 mg of Raney® nickel was added and the reaction was shaken an additional 2 h under 50 psi H2. The reaction mixture was filtered through Celite®, concentrated in vacuo and purified via column chromatography to afford 2′-amino-4′-(trifluoromethyl)-[1,1′-biphenyl]-3-acetic acid ethyl ester (58 mg, 59% yield). MS (ESI) m/z: 324.2 (M+H+).

Workup

  1. stirringthe reaction was shaken an additional 2 h under 50 psi H2
  2. filtrationThe reaction mixture was filtered through Celite®
  3. concentrationconcentrated in vacuo
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-c600d7184ba1462eb391f10f30effa94
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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