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

HRID 2077777Notes

Reaction equation

HRID 2077777 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-1638aad011dc4a8eaa8c1408ce152c40
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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