3-Amino-2-naphthoic acid → (3-Aminonaphthalen-2-yl)methanol

HRID 1642606Notes

Reaction equation

HRID 1642606 reaction equation
[NH2:1][C:2]1[C:3]([C:12](O)=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2>C1COCC1>[NH2:1][C:2]1[C:3]([CH2:12][OH:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

3

Reactant 1

HCID 222443-Amino-2-naphthoic acid

Product 1

HCID 10374898(3-Aminonaphthalen-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-2-naphthoic acid (2 g, 10.7 mmol) in THF (11 mL) at 0° C. is added a 1 M solution of borane-tetrahydrofuran complex (27 mL) dropwise over 15 min. The mixture is allowed to warm to ambient temperature and stirred for 6 h. The excess borane-tetrahydrofuran complex is quenched by adding methanol at 0° C., and the solvent evaporated to obtain a yellow solid. The solid is washed with water, EtOAc and then dried under high vacuum to give (3-aminonaphthalen-2-yl)-methanol.

Workup

  1. customThe excess borane-tetrahydrofuran complex is quenched
  2. additionby adding methanol at 0° C.
  3. customthe solvent evaporated
  4. customto obtain a yellow solid
  5. washThe solid is washed with water, EtOAc
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-22a0acca59f44533955a3995f360cc13
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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