Ethanol → 3-{2-[4-(Acetylamino)phenoxy]ethyl} 5-methyl 4-{3-nitrophenyl}-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate

HRID 4579

Reaction equation

HRID 4579 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](C=C[CH:30]=1)[CH:7]=[CH:8][C:9]([CH2:11][C:12]([O:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=1)=[O:13])=O)([O-:3])=[O:2].[NH2:31]/[C:32](/[CH3:38])=[CH:33]\[C:34]([O:36][CH3:37])=[O:35].[CH2:39](O)[CH3:40]>>[CH3:39][C:40]1[NH:31][C:32]([CH3:38])=[C:33]([C:34]([O:36][CH3:37])=[O:35])[CH:9]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:30]=2)[C:11]=1[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:22][CH:23]=1)=[O:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 643918Methyl 3-aminocrotonateHCID 573157372-(4-Acetylaminophenoxy)ethyl 2-(3-nitrobenzylidene)acetylacetate

Product 1

HCID 43288653-{2-[4-(Acetylamino)phenoxy]ethyl} 5-methyl 4-{3-nitrophenyl}-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylateYield 68%

Conditions

Temperature
7 °C

Procedure

15 g (0.04 moles) of 2-(4-acetylaminophenoxy)-ethyl 2-(3-nitrobenzilidene)acetylacetate and 4.19 g (0.04 moles) of methyl 3-aminocrotonate are heated for 4 hours under reflux in 40 ml of ethanol. The solution is cooled to 7° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as yellow crystals melting--after recrystallisation in isopropanol--at 202°-204° C. The yield was 68% of the theoretical yield.

Sources & evidence

ORD record
ord-2f8180b087294f358a57f119070003e4
Source dataset
uspto-grants-1988_02
Patent number
US04727066

Linked notes

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