Water → b-Amino-4-nitrobenzenepropanol

HRID 420855Notes

Reaction equation

HRID 420855 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N+:7]([C:10]1[CH:21]=[CH:20][C:13]([CH2:14][CH:15]([C:17](O)=[O:18])[NH2:16])=[CH:12][CH:11]=1)([O-:9])=[O:8].O.[OH-].[Na+]>O1CCCC1>[NH2:16][CH:15]([CH2:14][C:13]1[CH:20]=[CH:21][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=1)[CH2:17][OH:18]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 650894-NitrophenylalanineHCID 21226445Aluminium lithium hydride

Product 1

HCID 22634999b-Amino-4-nitrobenzenepropanolYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (271 mg) was suspended in tetrahydrofuran, the suspension was added with 4-nitro-DL-phenylalanine (1.0 g) under ice cooling, and the mixture was stirred for 1 hour. The reaction mixture was added successively with distilled water, 15% aqueous sodium hydroxide and distilled water, and the mixture was stirred for 12 hours. The reaction mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain the title compound (516 mg).

Workup

  1. distillationdistilled water
  2. stirringthe mixture was stirred for 12 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e6d55863faa4e48808ae92e577d33c9
Source dataset
uspto-grants-2012_01
Patent number
US08097708B2

Reaction notes

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