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

HRID 1982247Notes

Reaction equation

HRID 1982247 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]CC(=O)CC([O-])=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:18]([CH3:24])=[C:19]([C:20]([O:22][CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)=[O:21])[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 867408572-(4-Hydroxyphenyl)-ethylacetoacetate

Product 1

HCID 201974812,6-Dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-hydroxyphenyl)ethoxycarbonyl]-1,4-dihydropyridineYield 130.5%

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-aminocrotonate, 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. Calculated for C24H24N2O7.1.5H2O: C-60.12, H-5.68, N-5.84. Found: C-60.55, H-5.33, N-6.03.

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-2b713b7619434130b2c93843daba24aa
Source dataset
uspto-grants-1986_06
Patent number
US04595690

Reaction notes

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