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

HRID 557398Notes

Reaction equation

HRID 557398 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](/[CH3:29])=[CH:26]\[C:27]#[N:28].C(O)(=O)C>CC(O)C>[C:27]([C:26]1[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]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([CH3:23])[NH:24][C:25]=1[CH3:29])#[N:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 15979088Ethyl 5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-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 69.1 mg (0.53 mmol) of ethyl 3-oxobutanoate, 43.6 mg (0.53 mmol) of 3-aminocrotononitrile and 31.9 mg (0.53 mmol) of acetic acid in 5 ml of 2-propanol and heated under reflux under argon for 4 h. After cooling to room temperature, the crystallized product is filtered off and washed with 2-propanol and diethyl ether. 43 mg (22% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 4 h
  3. filtrationthe crystallized product is filtered off
  4. washwashed with 2-propanol and diethyl ether

Sources & evidence

ORD record
ord-f3aebd9de87943c79bc7beb66e2af587
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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