Ammonium formate → 3'-Amino-5'-fluoro-2'-hydroxy-biphenyl-3-carboxylic acid

HRID 384295Notes

Reaction equation

Br.[N+:2]([C:5]1[C:6]([OH:21])=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=2)[CH:8]=[C:9]([F:11])[CH:10]=1)([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:2][C:5]1[C:6]([OH:21])=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([OH:20])=[O:19])[CH:13]=2)[CH:8]=[C:9]([F:11])[CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3′-Nitro-5′-fluoro-2′-hydroxy-biphenyl-3-carboxylic acid hydrobromide 2e (417 mg, 1.5 mmol) was dissolved in 60 mL of ethanol followed by addition of 0.5 g of palladium on carbon and ammonium formate (0.95 g, 1.5 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 3′-amino-5′-fluoro-2′-hydroxy-biphenyl-3-carboxylic acid 2f (339 mg, yield 91.5%) as a purple solid.

Workup

temperatureThe reaction mixture was heated
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customdried

Sources & evidence

ORD record: ord-cb83fc022dd14e93ae63ccda1bd5d79f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367710B2

Reaction notes

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