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3-(4-Aminophenyl)propionic acid → 4-Aminobenzenepropanol

HRID 28611
Notes
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Reaction equation

HRID 28611 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 754513-(4-Aminophenyl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2204244-AminobenzenepropanolYield 89%

Procedure

To a mixture of 3-(4-amino-phenyl)-propionic acid (1.85 g, 11.2 mmol) and tetrahydrofuran′(200 ml), was added lithium aluminum hydride (1.0 g, 26 mmol). After stirring for 3 hours, the mixture was quenched by addition of methanol (5 ml) and concentrated under reduced pressure. The residue was treated with saturated aqueous sodium chloride solution (100 ml) and extracted with ethyl acetate (200 ml). The organic extract was concentrated under reduced pressure to give 3-(4-amino-phenyl)-propan-1-ol (1.5 g, 89% yield).

Workup

  1. customthe mixture was quenched by addition of methanol (5 ml)
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was treated with saturated aqueous sodium chloride solution (100 ml)
  4. extractionextracted with ethyl acetate (200 ml)
  5. extractionThe organic extract
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-2d30637f3a09471486294a64214e35e3
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07419984B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes