Methanol → (2-Amino-3-nitrophenyl)methanol

HRID 1012062Notes

Reaction equation

HRID 1012062 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[BH4-].[Na+].B(F)(F)F.CCOCC.CO>C1COCC1>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 2196332-Amino-3-nitrobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 10797172(2-Amino-3-nitrophenyl)methanolYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-3-nitrobenzoic acid (1.82 g, 10.0 mmol) in anhydrous THF (50 ml) was added sodium borohydride (770 mg, 20.0 mmol) followed by boron trifluoride diethyl etherate (2.5 ml, 20 mmol) and the mixture stirred at ambient temperature under a nitrogen atmosphere for 2 h. MeOH was cautiously added until gas evolution had ceased and the mixture reduced in vacuo. The residue was partitioned between EtOAc and brine and the organic portion dried (MgSO4) and reduced in vacuo to give 2-amino-3-nitrobenzyl alcohol (1.42 g) as a yellow solid.

Workup

  1. customThe residue was partitioned between EtOAc and brine
  2. dry with materialthe organic portion dried (MgSO4)

Sources & evidence

ORD record
ord-1ed9972a0c56401ba7c1a21af3ee10eb
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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