3-Nitrobenzaldehyde → 1,4-Dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridine

HRID 1762465Notes

Reaction equation

HRID 1762465 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].[CH3:12][O:13][C:14](=[O:19])/[CH:15]=[C:16](\[NH2:18])/[CH3:17].[C:20]([O:26][CH2:27][CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39])(=[O:25])[CH2:21][C:22]([CH3:24])=O>CC(O)C>[CH3:24][C:22]1[NH:18][C:16]([CH3:17])=[C:15]([C:14]([O:13][CH3:12])=[O:19])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:21]=1[C:20]([O:26][CH2:27][CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39])=[O:25]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 114031062-Phthalimidoethyl acetoacetate

Product 1

HCID 137998311,4-Dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridineYield 30%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 3.02 g (0.02 mol) of 3-nitrobenzaldehyde, 2.36 g (0.02 mol) of methyl-3-aminocrotonate, and 5.72 g (0.02 mol) of 2-phthalimidoethyl acetoacetate 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 dichloromethane/hexane). The product was isolated and recrystallized from 1:1 dichloromethane/hexane to yield 3.0 g (30%) of a pale yellow solid; m.p. 181.5°-182.5° C. NMR: (CDCl3); δ 2.3 (6H,s), 3.5 (3H,s), 3.9 (2H,m), 4.2 (2H,m), 4.9 (1H,s), 6.0 (1H,s), 7.0-8.0 (8H,m).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe product was isolated
  3. customrecrystallized from 1:1 dichloromethane/hexane

Sources & evidence

ORD record
ord-fe29c36cb1a74ab0bdf53ec1f0fababb
Source dataset
uspto-grants-1989_05
Patent number
US04833150

Reaction notes

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