3-Nitrobenzaldehyde → 2,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-hydroxyphenyl)ethoxycarbonyl]-1,4-dihydropyridine

HRID 652545Notes

Reaction equation

HRID 652545 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13]([CH3:15])=O)=[CH:4][CH:3]=1.[NH2:17]/[C:18](/[CH3:24])=[CH:19]\[C:20]([O:22][CH3:23])=[O:21].[N+:25]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH:31]=O)([O-:27])=[O:26]>CO>[CH3:24][C:18]1[NH:17][C:13]([CH3:15])=[C:12]([C:11]([O:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)=[O:16])[CH:31]([C:30]2[CH:33]=[CH:34][CH:35]=[C:28]([N+:25]([O-:27])=[O:26])[CH:29]=2)[C:19]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 1317151812-(4-Hydroxyphenyl)ethylacetoacetate

Product 1

HCID 201974812,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-hydroxyphenyl)ethoxycarbonyl]-1,4-dihydropyridineYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.3 g of 2-(4-hydroxyphenyl)ethylacetoacetate (10), 2.3 g of methyl β-amino-crotonate, 2.9 g of 3-nitrobenzaldehyde and 70 mL of methanol was heated at reflux for 12 hours. The solvent was removed under reduced pressure and the residue purified by silica gel chromatography using 50:50 ethyl acetate-hexane to yield 5.9 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-hydroxyphenyl)ethoxycarbonyl]-1,4-dihydropyridine (11), as an amorphous solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-5134a2b0a9b246cdb01bcb25f7cdb430
Source dataset
uspto-grants-1987_06
Patent number
US04672071

Reaction notes

Loading…