Ethanol → 3,3,5-Trimethylcyclohexyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

HRID 4585

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6](C=C[CH:26]=1)[CH:7]=[CH:8][C:9]([CH2:11][C:12]([O:14][CH:15]1[CH2:20][CH:19]([CH3:21])[CH2:18][C:17]([CH3:23])([CH3:22])[CH2:16]1)=[O:13])=O)([O-:3])=[O:2].[NH2:27]/[C:28](/[CH3:35])=[CH:29]\[C:30]([O:32][CH2:33][CH3:34])=[O:31].[CH2:36](O)[CH3:37]>>[CH3:36][C:37]1[NH:27][C:28]([CH3:35])=[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:9]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:26]=2)[C:11]=1[C:12]([O:14][CH:15]1[CH2:20][CH:19]([CH3:21])[CH2:18][C:17]([CH3:22])([CH3:23])[CH2:16]1)=[O:13]

Participants

Reactant 3

HCID 702Ethanol

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

HCID 704164953,3,5-Trimethylcyclohexyl 2-(3-nitrobenzylidene)acetylacetate

Product 1

HCID 201512113,3,5-Trimethylcyclohexyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylateYield 37%

Conditions

Temperature: -5 °C

Procedure

21.87 g (0.06 moles) of 3,3,5-trimethylcyclohexyl 2-(3-nitrobenzylidene)acetylacetate and 7.84 g (0.06 moles) of ethyl 3-aminocrotonate are heated under reflux in 60 ml of ethanol for 8 hours. The solution is then cooled to -5° C. to obtain 3,3,5-trimethylcyclohexyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as yellow crystals melting--after recrystallisation in ethanol--at 125°-129° C. The yield is 37% of the theoretical yield.

Sources & evidence

ORD record: ord-9f0b0ca41b4b431daa1c7c12af0a959b
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04727066

Linked notes

Loading…