3-Nitrobenzaldehyde → Cyclopentyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(3-nitrophenyl)-pyridine-5-carboxylate

HRID 371413Notes

Reaction equation

HRID 371413 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].[NH2:12]/[C:13](/[CH3:23])=[CH:14]\[C:15]([O:17][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:16].[N+:24]([CH2:27][C:28](=O)[CH3:29])([O-:26])=[O:25]>C(O)C>[CH3:29][C:28]1[NH:12][C:13]([CH3:23])=[C:14]([C:15]([O:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:16])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:27]=1[N+:24]([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 662962-Propanone, 1-nitro-HCID 57475511Cyclopentyl beta-aminocrotonate

Product 1

HCID 13121183Cyclopentyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(3-nitrophenyl)-pyridine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15.1 g (0.1 mol) of 3-nitrobenzaldehyde, together with 16.9 g (0.1 mol) of cyclopentyl β-aminocrotonate and 10.3 g (0.1 mol) of nitroacetone in 150 ml of ethanol, were heated under reflux for 6 hours. After the reaction mixture had cooled, the solvent was distilled off in vacuo, and the oily residue was taken up in a small amount of chloroform and was chromatographed on a silica gel column, using chloroform with the addition of methanol. The fractions containing the reaction product were concentrated, the residue was taken up in a small amount of isopropanol, and the nitrodihydropyridine crystallized in yellow crystals of melting point 174° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureAfter the reaction mixture had cooled
  3. distillationthe solvent was distilled off in vacuo
  4. customwas chromatographed on a silica gel column
  5. additionwith the addition of methanol
  6. additionThe fractions containing the reaction product
  7. concentrationwere concentrated
  8. customthe nitrodihydropyridine crystallized in yellow crystals of melting point 174° C.

Sources & evidence

ORD record
ord-bb144d23254d46838030790e72d1c330
Source dataset
uspto-grants-1985_07
Patent number
US04532248

Reaction notes

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