2-Hydroxy-3''-nitro-biphenyl-3-carboxylic acid → 3-(3-Amino-2-hydroxyphenyl)benzoic acid

HRID 910336Notes

Reaction equation

HRID 910336 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([OH:19])=[O:18])[CH:12]=1>CO.[Pd]>[NH2:8][C:7]1[C:2]([OH:1])=[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([OH:19])=[O:18])[CH:12]=2)[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 225057122-Hydroxy-3''-nitro-biphenyl-3-carboxylic acid

Product 1

HCID 114923323-(3-Amino-2-hydroxyphenyl)benzoic acidYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2′-hydroxy-3′-nitrobiphenyl-3-carboxylic acid (800 g, 3.2 mol) in methanol (5 L) was hydrogenated over 5% Pd/C (160 g) at room temperature for 8 hours. The reaction mixture was filtered, concentrated and slurried in THF (2.5 L) to give 3′-amino-2′-hydroxybiphenyl-3-carboxylic acid (690 g, 50.5%) as a brown solid. PXRD analysis provided the diffractogram as shown in FIG. 32.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9ec92d8b61344cff9ab9300e91cf81dd
Source dataset
uspto-grants-2011_09
Patent number
US08022093B2

Reaction notes

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