Hydrogen Bromide → 3'-Amino-2'-hydroxy-biphenyl-3-carboxylic acid hydrobromide

HRID 384288Notes

Reaction equation

C[O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=1.[BrH:19]>>[BrH:19].[NH2:9][C:8]1[C:3]([OH:2])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 574837863'-Amino-2'-methoxy-[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 574837893'-Amino-2'-hydroxy-biphenyl-3-carboxylic acid hydrobromideYield 88.8%

Conditions

Temperature: 120 °C

Procedure

2′-Methoxy-3′-amino-biphenyl-3-carboxylic acid 1e (2.5 g, 10.3 mmol) was dissolved in 100 mL of hydrobromic acid (40%). The reaction mixture was heated to reflux at 120° C. overnight, and the reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound 3′-amino-2′-hydroxy-biphenyl-3-carboxylic acid hydrobromide 1f (2.4 g, 88.8%) as a khaki solid.

Workup

temperatureThe reaction mixture was heated
concentrationThe mixture was concentrated under reduced pressure
customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-4ed6f6d4269745d3aa02de2610da7d69
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367710B2

Reaction notes

Loading…