(2-Amino-3-nitrophenyl)methanol → (2,3-Diaminophenyl)methanol

HRID 1012063Notes

Reaction equation

HRID 1012063 reaction equation
[NH2:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]>CCO.CN(C=O)C.[Pd]>[NH2:1][C:2]1[C:9]([NH2:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 1

HCID 10797172(2-Amino-3-nitrophenyl)methanol

Product 1

HCID 1514188(2,3-Diaminophenyl)methanolYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-3-nitrobenzyl alcohol (1.4 g) and 10% Pd/C (140 mg) in EtOH (40 ml) and DMF (10 ml) was stirred under an atmosphere of hydrogen at ambient temperature for 18 h. The catalyst was removed by filtration through Celite, the filtrate reduced in vacuo and azeotroped with toluene (2×50 ml) to give 2,3-diaminobenzyl alcohol (1.15 g) as a dark brown solid.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customazeotroped with toluene (2×50 ml)

Sources & evidence

ORD record
ord-bb328f82cb174263ae26a3bd42246001
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

Loading…