Hydrochloric Acid → HCID 19980527, compound

HRID 231124Notes

Reaction equation

[C:1]1([CH:7]2[CH2:9][CH:8]2[C:10](=O)[C:11](=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:28]([O:30][C:31](=[O:36])/[CH:32]=[C:33](\[NH2:35])/[CH3:34])[CH3:29].Cl>CCO>[C:1]1([CH:7]2[CH2:9][CH:8]2[C:10]2[NH:35][C:33]([CH3:34])=[C:32]([C:31]([O:30][CH2:28][CH3:29])=[O:36])[CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)[C:11]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl 3-(2-phenyl-1-cyclopropyl)-2-(m-nitrophenylmethylen)-3-oxo-propanoate (5 g) and ethyl-3-aminocrotonate (1.6 g) in EtOH (50 ml) is heated to the reflux temperature for 4 hours, then it is cooled at 0° C., acidified with concentrated aqueous HCl (0.2 ml) and stirred at 0° C. for 30 minutes. After neutralization with a few drops of a saturated Na2HPO4 water solution, the mixture is evaporated and the residue is dissolved in AcOEt (60 ml), washed with water (3×10 ml), dried on Na2SO4 and purified on silica gel (200 g, eluent: diisopropylether/Et ether/Et2O 80/20) to give 4.0 g of 2-(2-phenyl-1-cyclopropyl)-3,5-dicarboethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine amorphous solid.

Workup

customAfter neutralization with a few drops of a saturated Na2HPO4 water solution, the mixture is evaporated
dissolutionthe residue is dissolved in AcOEt (60 ml)
washwashed with water (3×10 ml)
customdried on Na2SO4
custompurified on silica gel (200 g, eluent: diisopropylether/Et ether/Et2O 80/20)

Sources & evidence

ORD record: ord-25a8b17921cc4dc69b6ebe167608e7c1
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845113

Reaction notes

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