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

HRID 557394Notes

Reaction equation

HRID 557394 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]([CH3:24])[CH2:17][C:18]([O:20][CH2:21][CH2:22][CH3:23])=[O:19].[NH2:25]/[C:26](/[CH3:30])=[CH:27]\[C:28]#[N:29].C(O)(=O)C>CC(O)C>[C:28]([C:27]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][CH2:22][CH3:23])=[O:19])=[C:16]([CH3:24])[NH:25][C:26]=1[CH3:30])#[N:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 74507Propyl acetoacetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 15978970Propyl 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

700 mg (3.7 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 536 mg (3.7 mmol) of propyl 3-oxobutanoate, 205 mg (3.7 mmol) of 3-aminocrotononitrile and 223 mg (3.7 mmol) of acetic acid in 20 ml of 2-propanol and heated under reflux under argon for 16 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 460 mg (32% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 16 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-90acb69e3fdc4745b516d1f41204dca9
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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