3-Amino-5-nitrobenzoic acid → (3-Amino-5-nitrophenyl)methanol

HRID 254942

Reaction equation

HRID 254942 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5](O)=[O:6]>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1

Participants

3

Reactant 1

HCID 2393423-Amino-5-nitrobenzoic acid

Product 1

HCID 15540036(3-Amino-5-nitrophenyl)methanolYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-5-nitrobenzoic acid (1.12 g, 6.16 mmol) in THF (5 mL) was added dropwise a solution of borane tetrahydrofuran complex solution (13.6 mL, 13.6 mmol) at ambient temperature and the mixture was stirred for 90 minutes. The solvent was then evaporated. Aqueous NaOH (15 mL) was added and the resulting mixture was extracted with ether. The ether solution was dried over anhydrous Na2SO4. Evaporation of ether afforded 921 mg of the title compound (89%).

Workup

  1. customThe solvent was then evaporated
  2. additionAqueous NaOH (15 mL) was added
  3. extractionthe resulting mixture was extracted with ether
  4. dry with materialThe ether solution was dried over anhydrous Na2SO4
  5. customEvaporation of ether

Sources & evidence

ORD record
ord-e35f272e72554c879e05fbbc6fa22fd1
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Linked notes

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