Ammonium formate → 5-Amino-biphenyl-2-carboxylic acid methyl ester

HRID 2121184Notes

Reaction equation

HRID 2121184 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 15406987Methyl 5-nitrobiphenyl-2-carboxylate

Product 1

HCID 154069885-Amino-biphenyl-2-carboxylic acid methyl esterYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the 2-phenyl-4-nitrobenzoic acid methyl ester prepared in Example 210A (48.4 g, 188 mmol), palladium (10%) on carbon (2.1 g), and ammonium formate (59.4 g, 941 mmol) in methanol (500 mL) was refluxed for 3 hours. The solvent was removed in vacuo, and the residue was desolved in a miminum amount of hot methanol (about 30 mL). To this solution was added chloroform and ether (1/1 ratio, 400 mL), and the mixture was filtered through a plug of silica gel (80 g) and rinsed with chloroform. The filtrate was concentrated in vacuo to give pure 2-phenyl-4-aminobenzoic acid methyl ester (42.4 g, 99%). 1H NMR (300 MHz, CDCl3) δ 7.80 (d, 1H), 7.40-7.25 (m, 5H), 6.65 (dd, 1H), 6.57 (d, 1H), 3.60 (s 3H).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe solvent was removed in vacuo
  3. additionTo this solution was added chloroform and ether (1/1 ratio, 400 mL)
  4. filtrationthe mixture was filtered through a plug of silica gel (80 g)
  5. washrinsed with chloroform
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-263e5c441f144d9bb345bde5b7b0d98c
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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