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

HRID 371414Notes

Reaction equation

HRID 371414 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].[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH3:24])(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:25][C:26]([CH3:31])=[CH:27][N+:28]([O-:30])=[O:29]>C(O)C>[CH3:31][C:26]1[NH:25][C:14]([CH3:16])=[C:13]([C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH3:24])=[O:17])[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+:28]([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 12529182Butanoic acid, 3-oxo-, 2-propoxyethyl esterHCID 714047121-Nitroprop-1-en-2-amine

Product 1

HCID 13121184beta-n-Propoxyethyl 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 18.8 g (0.1 mol) of β-n-propoxyethyl acetoacetate and 10.2 g (0.1 mol) of 2-amino-1-nitro-prop-1-ene in 150 ml of ethanol, were heated uder reflux for 6 hours. After cooling, 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 product were concentrated, the residue was taken up in a small amount of isopropanol, and the nitrodihydropyridine crystallized in yellow crystals of melting point 161° C.

Workup

  1. temperatureuder reflux for 6 hours
  2. temperatureAfter cooling
  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 product
  7. concentrationwere concentrated
  8. customthe nitrodihydropyridine crystallized in yellow crystals of melting point 161° C.

Sources & evidence

ORD record
ord-8208e739b691472291e8e626a5fd3667
Source dataset
uspto-grants-1985_07
Patent number
US04532248

Reaction notes

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