Ammonium formate → 3'-Amino-2'-methoxy-[1,1'-biphenyl]-3-carboxylic acid

HRID 384287Notes

Reaction equation

HRID 384287 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 98567672'-Methoxy-3'-nitrobiphenyl-3-carboxylic acid

Product 1

HCID 574837863'-Amino-2'-methoxy-[1,1'-biphenyl]-3-carboxylic acidYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2′-Methoxy-3′-nitro-biphenyl-3-carboxylic acid 1d (0.48 g, 1.74 mmol) was dissolved in 60 mL of ethanol followed by addition of 0.5 g of palladium on carbon and ammonium formate (1.1 g, 17.4 mmol). The reaction mixture was heated to reflux at 80° C. for 20 minutes. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filtrate was concentrated under reduced pressure and dried to obtain the title compound 2′-methoxy-3′-amino-biphenyl-3-carboxylic acid 1e (0.42 g, yield 93.3%) as a white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customdried

Sources & evidence

ORD record
ord-bcc82b375ad44d67931a70508beed724
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

Loading…