Acetic Acid → n-Propyl 5-acetyl-4-(5-chloro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylate

HRID 1669779Notes

Reaction equation

HRID 1669779 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[C:8]2[C:3]=1[C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[O:7]2.[CH3:16][C:17](=O)[CH2:18][C:19](=[O:21])[CH3:20].[NH2:23]/[C:24](/[CH3:32])=[CH:25]\[C:26]([O:28][CH2:29][CH2:30][CH3:31])=[O:27].C(O)(=O)C>CC(O)C>[C:19]([C:18]1[CH:12]([C:9]2[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]3[C:8]=2[O:7][C:6]([CH3:14])=[CH:5][C:4]3=[O:15])[C:25]([C:26]([O:28][CH2:29][CH2:30][CH3:31])=[O:27])=[C:24]([CH3:32])[NH:23][C:17]=1[CH3:16])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31261AcetylacetoneHCID 12706963Propyl 3-aminobut-2-enoateHCID 574388945-Chloro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 57503339n-Propyl 5-acetyl-4-(5-chloro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

40 mg (0.18 mmol) of 5-chloro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 31 mg (0.18 mmol) of 2,4-pentanedione, 25 mg (0.18 mmol) of n-propyl 3-aminocrotonate and 11 mg (0.18 mmol) of acetic acid in 2 ml of 2-propanol and heated under reflux under argon for 10 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. 33 mg (42% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 10 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-135702a762244620ae4b88036cc92951
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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