Acetic Acid → Ethyl 2,6-dimethyl-5-(4-methylbenzoyl)-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-pyridine-3-carboxylate

HRID 1669803Notes

Reaction equation

HRID 1669803 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.O=[C:16]([CH3:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[NH2:24][C:25]([CH3:36])=[CH:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)=[O:28].C(O)(=O)C>CC(O)C>[CH3:23][C:16]1[NH:24][C:25]([CH3:36])=[C:26]([C:27](=[O:28])[C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 673437903-Amino-1-(4-methylphenyl)but-2-en-1-one

Product 1

HCID 57503357Ethyl 2,6-dimethyl-5-(4-methylbenzoyl)-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

100 mg (0.53 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 69 mg (0.53 mmol) of ethyl 3-oxobutanoate, 93 mg (0.53 mmol) of 3-amino-1-(4-methylphenyl)but-2-en-1-one and 3 μl (0.05 mmol) of acetic acid in 5 ml of 2-propanol and heated under reflux under argon for 30 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 180 mg (74% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 30 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-795744b12b6545a29ac407c6337a6899
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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