Isopropanol → 2,6-Dimethyl-3-(2-phthalimidocarbethoxy)-4-(3-methylphenyl)-5-carbomethoxy-1,4-dihydropyridine

HRID 1762464Notes

Reaction equation

HRID 1762464 reaction equation
[C:1]([O:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[CH3:21][O:22][C:23](=[O:28])/[CH:24]=[C:25](\[NH2:27])/[CH3:26].[CH3:29][CH:30](O)[CH3:31]>>[CH3:5][C:3]1[NH:27][C:25]([CH3:26])=[C:24]([C:23]([O:22][CH3:21])=[O:28])[CH:29]([C:30]2[CH:31]=[CH:18][CH:19]=[C:12]([CH3:13])[CH:11]=2)[C:2]=1[C:1]([O:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])=[O:6]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 643918Methyl 3-aminocrotonateHCID 114031062-Phthalimidoethyl acetoacetate

Product 1

HCID 137998302,6-Dimethyl-3-(2-phthalimidocarbethoxy)-4-(3-methylphenyl)-5-carbomethoxy-1,4-dihydropyridineYield 50%

Procedure

A solution of 7.0 g (0.25 mol) of 2-phthalimidoethyl acetoacetate and 3.1 g (0.025 mol) of methyl3-aminocrotonate in 150 ml of 2-propanol was refluxed for 15 hours under nitrogen. The solvent was removed in vacuo and the residue was subjected to flash chromatography (silica gel, 1:1 petroleum ether/ethyl acetate). The isolated product was recrystallized in dichloromethane/hexane to give 3.5 g (50%) of a pale yellow solid; m.p. 188°-190° C. NMR: (CDCl3) δ 2.1 (9H,d), 3.5 (3M,s), 3.7 (2H,m), 4.2 (2H,m), 4.6 (1H,s), 5.8 (1H,s), 7.2 (8H,m).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe isolated product was recrystallized in dichloromethane/hexane

Sources & evidence

ORD record
ord-c0ce4b8bce2d444196931ef321b896e1
Source dataset
uspto-grants-1989_05
Patent number
US04833150

Reaction notes

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