Hydrochloric Acid → HCID 12646051, compound

HRID 1402929Notes

Reaction equation

HRID 1402929 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].[ClH:15]>C(O)C>[Cl:15][C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH2:10][CH2:9][C:8]([O:12][CH2:13][CH3:14])=[O:11])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8821Ethyl Acrylate

Product 1

HCID 12646051HCID 12646051, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of aniline (1.4 ml), ethyl acrylate (3.4 ml), and conc. HCl (1.6 ml) in ethanol (17 ml) was heated to reflux for 24 h. Then the solvent was removed and the residue partitioned between an excess of ammonia solution and dichloromethane. The organic layer was separated, washed with brine, dried (MgSO4), and evaporated. The residue was purified by flash chromatography on silica gel (hexane/ethyl acetate 2:1) to provide ethyl N-(4-chlorophenyl)-3-aminopropionate (1.27 g) as yellowish oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. customThen the solvent was removed
  4. customthe residue partitioned between an excess of ammonia solution and dichloromethane
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica gel (hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-40a8db4f35c94e83b1b6286c9921c03c
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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