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

HRID 1444717

Reaction equation

HRID 1444717 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-]>C1COCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 2204244-Aminobenzenepropanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an oven-dried 150 mL round-bottomed flask charged with 3-(4-aminophenyl)propionic acid (Aldrich, 3.0 g, 18.16 mmol) was added THF (50 mL) and lithium aluminum hydride (Aldrich, 1.0M THF solution, 37 mL, 36.32 mmol) at 0° C. The reaction mixture was added Na2SO4.10H2O after 3 h until there was no visible bubbles. The liquid was filtered. The solid was washed with THF and CH2Cl2. The filtrate was dried over Na2SO4. After filtration and concentration in vacuo, the crude was purified by flash chomatography (7% MeOH—CH2Cl2) to provide the title product. MS (ESI): 152 (M+H)+.

Workup

  1. filtrationThe liquid was filtered
  2. washThe solid was washed with THF and CH2Cl2
  3. dry with materialThe filtrate was dried over Na2SO4
  4. filtrationAfter filtration and concentration in vacuo
  5. customthe crude was purified by flash chomatography (7% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-0948143fff634beab2c395645f8ae67d
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Linked notes

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