5-Amino-2-nitrobenzoic acid → (5-Amino-2-nitrophenyl)methanol

HRID 133757Notes

Reaction equation

HRID 133757 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].B.O1CCCC1>O1CCCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH2:7][OH:8])[CH:10]=1

Participants

4

Reactant 2

HCID 832985-Amino-2-nitrobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 13238551(5-Amino-2-nitrophenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-amino-2-nitrobenzoic acid (3.0 g, 16.4 mmol) in 40 ml of tetrahydrofuran was added 50 ml of borane-tetrahydrofuran complex (1.0 M solution in THF). The mixture was heated under reflux for one hour. The usual workup afforded the product. 1H NMR (400 MHz, DMSO-d6): 4.79 (2H, d, J=5.4 Hz), 5.37 (1H, t, J=5.4 Hz), 6.48 (1H, dd, J=9.0 Hz, J=2.5 Hz), 6.68 (2H, s), 6.99 (1H, d, J=2.5 Hz), 7.94 (1H, d, J=9.0 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for one hour
  3. customThe usual workup afforded the product

Sources & evidence

ORD record
ord-2c7cfca3b86847e18dea970910d39666
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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