Aniline → beta-Alanine, N-phenyl-, ethyl ester

HRID 1034213Notes

Reaction equation

HRID 1034213 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:12][CH2:13][CH3:14])(=[O:11])[CH:9]=[CH2:10].[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[C:2]1([NH:1][CH2:10][CH2:9][C:8]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8821Ethyl AcrylateHCID 24287Tin tetrachloride

Product 1

HCID 10910393beta-Alanine, N-phenyl-, ethyl esterYield 60.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

According to the procedure of P. L. Southwick, J. Am. Chem. Soc. 75 3413 (1953), to a solution of aniline (31.86 g, 0.35 mol) and ethyl acrylate (35.0 g, 0.35 mol) in 200 ml of dry benzene (freshly distilled from CaH2) was added 0.5 ml of tin tetrachloride and the resulting solution was heated under reflux for 24 h. After cooling to room temperature the suspension was filtered to remove the inorganic solids and then concentrated in vacuo to give a dark green oil which was chromatographed on silica gel eluting with ethyl acetate/toluene (30/70) to give the title compound (40.7 g, 60%) as a light yellow oil. B.p. 95°-98° C. at 0.1 mm Hg.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 24 h
  3. filtrationwas filtered
  4. customto remove the inorganic solids
  5. concentrationconcentrated in vacuo
  6. customto give a dark green oil which
  7. customwas chromatographed on silica gel eluting with ethyl acetate/toluene (30/70)

Sources & evidence

ORD record
ord-404ac4db8d0542389e95e0e947bef759
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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