Water → (3-(2-Aminonaphthalen-1-yl)phenyl)methanol

HRID 1526159Notes

Reaction equation

HRID 1526159 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](O)=[O:16].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[CH:13]=[C:14]([CH2:15][OH:16])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 21226445Aluminium lithium hydrideHCID 585687123-(2-Aminonaphthalen-1-yl)benzoic acid

Product 1

HCID 58568731(3-(2-Aminonaphthalen-1-yl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 13.2 g (50 mmol) of 3-(2-aminonaphthalen-1-yl)benzoic acid in 300 ml of THF is added dropwise to a solution of 3.8 g (100 mmol) of lithium aluminium hydride in 500 ml of THF. When the addition is complete, the mixture is stirred under reflux for a further 2 h and allowed to cool, 4 ml of water, 4 ml of 15% by weight NAOH solution and 12 ml of water are then added dropwise, the mixture is stirred for a further 30 min., the precipitated salts are filtered off with suction and washed three times with 100 ml of THF each time, and the THF is removed in vacuo. Yield: 11.2 g (90 mmol), 89.8%; purity according to 1H-NMR about 95%.

Workup

  1. additionWhen the addition
  2. temperatureunder reflux for a further 2 h
  3. temperatureto cool
  4. stirringthe mixture is stirred for a further 30 min.
  5. filtrationthe precipitated salts are filtered off with suction
  6. washwashed three times with 100 ml of THF each time
  7. customthe THF is removed in vacuo

Sources & evidence

ORD record
ord-6179c4a5b5a44cbba46acec45b4e314d
Source dataset
uspto-grants-2015_07
Patent number
US09085579B2

Reaction notes

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