3-Nitrobenzaldehyde → 2,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenyl]ethoxycarbonyl)-1,4-dihydropyridine

HRID 652540Notes

Reaction equation

HRID 652540 reaction equation
[CH3:1][C:2]1([CH3:24])[O:6][CH:5]([CH2:7][O:8][CH:9]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22]C=[CH:20][CH:19]=2)C(=O)CC([O-])=O)[CH2:4][O:3]1.[NH2:25]/[C:26](/[CH3:32])=[CH:27]\[C:28]([O:30][CH3:31])=[O:29].[N+:33]([C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH:39]=O)([O-:35])=[O:34]>C(O)C>[CH3:32][C:26]1[NH:25][C:26]([CH3:32])=[C:27]([C:28]([O:30][CH2:22][CH2:23][C:18]2[CH:17]=[CH:16][C:9]([O:8][CH2:7][CH:5]3[CH2:4][O:3][C:2]([CH3:1])([CH3:24])[O:6]3)=[CH:20][CH:19]=2)=[O:29])[CH:39]([C:38]2[CH:41]=[CH:42][CH:43]=[C:36]([N+:33]([O-:35])=[O:34])[CH:37]=2)[C:27]=1[C:28]([O:30][CH3:31])=[O:29]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 1317151804-(2,2-Dimethyl-1,3-dioxolan-4-yl)methoxyphenylethylacetoacetate

Product 1

HCID 136325642,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenyl]ethoxycarbonyl)-1,4-dihydropyridineYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 13.2 g. (0.039 mol) of 4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenylethylacetoacetate (5), 4.7 g (0.41 mol) of methyl β-aminocrotonate, and 6.2 g (0.41 mol) of 3-nitrobenzaldehyde in 80 mL of ethanol was heated at reflux for 12 h. Solvent was removed in vacuo and the residue purified by medium pressure chromatography on silica gel (80% ether-hexane) to give 21 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenyl]ethoxycarbonyl)-1,4-dihydropyridine (6) as an orange oil.

Workup

  1. temperatureat reflux for 12 h
  2. customSolvent was removed in vacuo
  3. customthe residue purified by medium pressure chromatography on silica gel (80% ether-hexane)

Sources & evidence

ORD record
ord-510265164e6f43a8adc99ce73ad53a5d
Source dataset
uspto-grants-1987_06
Patent number
US04672071

Reaction notes

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