Ethyl 3-(4-chlorophenyl)-3-oxopropanoate → Methyl 6-(4-chlorophenyl)-2-ethyl-4-oxo-1,4-dihydropyridine-3-carboxylate

HRID 1099592Notes

Reaction equation

HRID 1099592 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12]CC)=O)=[CH:4][CH:3]=1.[NH2:16][C:17]([CH2:23][CH3:24])=[CH:18][C:19]([O:21][CH3:22])=[O:20]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:16][C:17]([CH2:23][CH3:24])=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:10](=[O:12])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 101336Ethyl 3-(4-chlorophenyl)-3-oxopropanoateHCID 57860398Methyl 3-aminopent-2-enoate

Product 1

HCID 25210929Methyl 6-(4-chlorophenyl)-2-ethyl-4-oxo-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2.00 g (8.82 mmol) of ethyl 3-(4-chlorophenyl)-3-oxopropanoate and 1.25 g (9.71 mmol) of methyl 3-aminopent-2-enoate [Pena et al., J. Am. Chem. Soc. 124, 14552-14553 (2002)] were taken up in 12 ml of xylene, 3.50 g molecular sieve (4 Å) which had been dried by heating were added and the mixture was reacted at reflux temperature overnight. The molecular sieve was removed by filtration and washed with methanol/chloroform (1/1). The combined organic phases were concentrated on a rotary evaporator and the crude product was purified by preparative MPLC (Biotage 40M cartridge; mobile phase: isohexane/ethyl acetate 4/1). This gave 550 mg (21% of theory) of the target compound.

Workup

  1. custom3.50 g molecular sieve (4 Å) which had been dried
  2. temperatureby heating
  3. additionwere added
  4. customthe mixture was reacted
  5. temperatureat reflux temperature overnight
  6. customThe molecular sieve was removed by filtration
  7. washwashed with methanol/chloroform (1/1)
  8. concentrationThe combined organic phases were concentrated on a rotary evaporator
  9. customthe crude product was purified by preparative MPLC (Biotage 40M cartridge; mobile phase: isohexane/ethyl acetate 4/1)

Sources & evidence

ORD record
ord-8f2b7d3675e14b01ab21ae7282d483e5
Source dataset
uspto-grants-2012_03
Patent number
US08143411B2

Reaction notes

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