Hydrochloric Acid → Ethyl 3-amino-3-(4-chlorophenyl)propanoate

HRID 1099589Notes

Reaction equation

HRID 1099589 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:11]C([O-])=O.C([O-])(=O)C.[NH4+:23].Cl>C(O)C>[NH2:23][CH:6]([C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:11][C:10]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 517165Ammonium AcetateHCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 2847357Ethyl 3-amino-3-(4-chlorophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g (71.1 mmol) of 4-chlorobenzaldehyde, 9.40 g (71.1 mmol) of monoethyl malonate and 10.9 g (142.3 mmol) of ammonium acetate were taken up in 60 ml of ethanol, and the mixture was stirred at reflux temperature overnight. After cooling, 50 ml 1N hydrochloric acid were added to the residue and the mixture was washed with ethyl acetate. The aqueous phase was made basic with potassium carbonate and then extracted with dichloromethane (2×). The organic phase was dried with magnesium sulfate and the solvent was removed on a rotary evaporator. The residue was purified by preparative HPLC (mobile phase: acetonitrile/water, gradient 10:90→90:10). This gave 1.80 g (11% of theory) of the target compound.

Workup

  1. temperatureat reflux temperature overnight
  2. temperatureAfter cooling
  3. washthe mixture was washed with ethyl acetate
  4. extractionextracted with dichloromethane (2×)
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. customthe solvent was removed on a rotary evaporator
  7. customThe residue was purified by preparative HPLC (mobile phase: acetonitrile/water, gradient 10:90→90:10)

Sources & evidence

ORD record
ord-cac3931f9e624592b30c773eb7bfd7e4
Source dataset
uspto-grants-2012_03
Patent number
US08143411B2

Reaction notes

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