Acetic Acid → Methyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(3-phenylquinolin-5-yl)-pyridine-5-carboxylate

HRID 2372824Notes

Reaction equation

HRID 2372824 reaction equation
[N+:1]([CH2:4][C:5](=O)[CH3:6])([O-:3])=[O:2].[NH2:8]/[C:9](/[CH3:15])=[CH:10]\[C:11]([O:13][CH3:14])=[O:12].C(O)(=O)C.[C:20]1([C:26]2[CH:27]=[N:28][C:29]3[CH:30]=[CH:31][CH:32]=[C:33]([CH:36]=O)[C:34]=3[CH:35]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH3:6][C:5]1[NH:8][C:9]([CH3:15])=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:36]([C:33]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:34]=2[CH:35]=[C:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=[N:28]3)[C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 662962-Propanone, 1-nitro-HCID 643918Methyl 3-aminocrotonateHCID 151703323-Phenylquinoline-5-carbaldehyde

Product 1

HCID 15170333Methyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(3-phenylquinolin-5-yl)-pyridine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.9 g (8.75 of nitroacetone, 0.58 g (5 mmol) of methyl 3-aminocrotonate and 0.3 ml (5 mmol) of acetic acid are added to 1.17 g (5 mmol) of 3-phenylquinoline-5-aldehyde in 10 ml of ethanol and the mixture is boiled for 1 hour. It is cooled and concentrated. The evaporation residue is purified by means of a silica gel column using chloroform/methanol mixtures. The clean fractions are concentrated, and the evaporation residue is recrystallized from ethyl acetate. 0.6 g of orange-colored crystals of melting point 262° C. are obtained.

Workup

  1. temperatureIt is cooled
  2. concentrationconcentrated
  3. customThe evaporation residue is purified by means of a silica gel column
  4. concentrationThe clean fractions are concentrated
  5. customthe evaporation residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fe7f6a44ab3142d581d76f09f7995da6
Source dataset
uspto-grants-1992_03
Patent number
US05100900

Reaction notes

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