Ethyl 2-(4-aminophenyl)propanoate → HCID 21876239, compound

HRID 858509Notes

Reaction equation

HRID 858509 reaction equation
C([O:3][C:4](=O)[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:6])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:13][C:10]1[CH:9]=[CH:8][C:7]([CH:5]([CH3:6])[CH2:4][OH:3])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 118009Ethyl 2-(4-aminophenyl)propanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 21876239HCID 21876239, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(4-amino-phenyl)-propionic acid ethyl ester (5.0 g, 25.9 mmol, Takahashi, I. et al., Heterocycles 1996, 43, 2343–2346.) in tetrahydrofurane (200 ml) was slowly added lithiumaluminium hydride (1.96 g, 51.8 mmol), and the mixture was stirred at room temperature for 14 h. The reaction mixture was quenched with 25% ammonia solution (50 ml) under ice-bath cooling. The resulting precipitate was filtered off, and the filtrate concentrated under reduced pressure to afford 3.88 g (99%) of the title compound as slight brown syrup.

Workup

  1. customThe reaction mixture was quenched with 25% ammonia solution (50 ml) under ice-bath
  2. temperaturecooling
  3. filtrationThe resulting precipitate was filtered off
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-5f3cba6394964b9392c9263b7e5e0cfe
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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