3-Nitrobenzaldehyde → 2,6-Dimethyl-3,5-di(2-phthalimidocarbethoxy)-4-(3-nitrophenyl)-1,4-dihydropyridine

HRID 1762466Notes

Reaction equation

HRID 1762466 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])(=[O:17])[CH2:13][C:14]([CH3:16])=O.[OH-:32].[NH4+:33]>CC(O)C>[CH3:16][C:14]1[NH:33][C:14]([CH3:16])=[C:13]([C:12]([O:18][CH2:19][CH2:20][N:21]2[C:22](=[O:31])[C:23]3=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]3[C:25]2=[O:26])=[O:32])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:13]=1[C:12]([O:18][CH2:19][CH2:20][N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])=[O:17]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 14923Ammonium HydroxideHCID 114031062-Phthalimidoethyl acetoacetate

Product 1

HCID 137998322,6-Dimethyl-3,5-di(2-phthalimidocarbethoxy)-4-(3-nitrophenyl)-1,4-dihydropyridine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 137 mg (0.9 m mol) of 3-nitrobenzaldehyde, 0.5 g (1.82 m mol) of 2-phthalimidoethyl acetoacetate, and 0.16 ml (2.4 m mol) of 14.7M ammonium hydroxide in 40 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, 3:1 petroleum ether/ethyl acetate) to yield 50 mg of pale yellow product; m.p. 92°-94° C.; NMR: (CDCl3) δ 2.2 (6M,s), 3.8 (4H,m), 4.2 (4H,m), 4.8 (1H,s), 6.1 (1H,s), 7.2 (12H,m).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ce3d0afba12b4038b30d9109d3ada454
Source dataset
uspto-grants-1989_05
Patent number
US04833150

Reaction notes

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