Methyl 3-nitro-5-phenylbenzoate → Methyl 5-amino-[1,1'-biphenyl]-3-carboxylate

HRID 1070405Notes

Reaction equation

HRID 1070405 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[C:9]([N+:11]([O-])=O)[CH:10]=1)=[O:4]>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:4]

Participants

4

Reactant 1

HCID 69687208Methyl 3-nitro-5-phenylbenzoate

Product 1

HCID 67513694Methyl 5-amino-[1,1'-biphenyl]-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Nitro-biphenyl-3-carboxylic acid methyl ester (1.85 g, 7.19 mmol) and 10% Pd/C (0.185 g) in EtOAc (20 mL) were hydrogenated under balloon for 2 h. The catalyst was filtered and the filtrate was concentrated to dryness. The crude 5-amino-biphenyl-3-carboxylic acid methyl ester was a yellow solid and was taken to the next step.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-e3e681e95c2d4e1c94cc267285ae05ee
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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