Water → 2-Amino-3-[hydroxy(phenyl)methyl]benzeneethanol

HRID 1589209Notes

Reaction equation

HRID 1589209 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[C:13]([C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:22][C:23](OCC)=[O:24].O.[OH-].[Na+]>O1CCCC1>[NH2:7][C:8]1[C:13]([CH:14]([OH:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:22][CH2:23][OH:24]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12901249Ethyl (2-amino-3-benzoylphenyl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 135776612-Amino-3-[hydroxy(phenyl)methyl]benzeneethanolYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 5.5 g (0.145 mole) of lithium aluminum hydride in 60 ml of dry tetrahydrofuran was treated with 19.4 g (0.0685 mole) of 2-amino-3-benzoyl benzeneacetic acid, ethyl ester dissolved in 120 ml of dry tetrahydrofuran stirred under nitrogen. After addition was complete, the mixture was continued at reflux for 2 hours. The mixture was then cooled, treated with successive additions of 5.5 ml of water, 5.5 ml of 15% sodium hydroxide and 16.5 ml of water. The mixture was then filtered, the filtrate stripped and the residue recrystallized from toluene. The titled compound (10.2 g) was obtained as pinkish needles,

Workup

  1. additionAfter addition
  2. temperatureat reflux for 2 hours
  3. temperatureThe mixture was then cooled
  4. filtrationThe mixture was then filtered
  5. customthe residue recrystallized from toluene

Sources & evidence

ORD record
ord-b717db53633f4361beaac35cd8d2831e
Source dataset
uspto-grants-1986_02
Patent number
US04568695

Reaction notes

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