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

HRID 238697Notes

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

Employing a known method outlined in patent application WO0189457: 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. 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-736d7ace2e9e4f18bc98395e403e2e73
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642637B2

Reaction notes

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