Methyl 3-(3-nitrophenyl)benzoate → (1,1'-Biphenyl)-3-carboxylic acid, 3'-amino-, methyl ester

HRID 1069078Notes

Reaction equation

HRID 1069078 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]>O1CCCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 1

HCID 11708671Methyl 3-(3-nitrophenyl)benzoate

Product 1

HCID 1394215(1,1'-Biphenyl)-3-carboxylic acid, 3'-amino-, methyl esterYield 111.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3′-nitro-[1,1′-biphenyl]-3-carboxylic acid methyl ester (4.47 g) in anhydrous tetrahydrofuran (125 mL) under a blanket of nitrogen was added 10% palladium on activated charcoal (860 mg). The reaction was evacuated and placed under a hydrogen atmosphere and stirred overnight. The reaction mixture was filtered through Celite and the solvent was removed under reduced pressure to yield a gray oil (4.4 g). The residue was chromatographed on silica eluting with 3:1 hexane:ethyl acetate. Concentration of the appropriate fractions provided the title compound as a white solid (3.5 g).

Workup

  1. customThe reaction was evacuated
  2. filtrationThe reaction mixture was filtered through Celite
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1642284da67440b8bdf4b76884dd8663
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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