HCID 54296870, compound → 1,4-Dihydro-2,6-dimethyl-3,5-dinitro-4-(3-nitrophenyl)pyridine

HRID 371415Notes

Reaction equation

HRID 371415 reaction equation
[N+:1]([C:4]([C:15](=O)[CH3:16])=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)([O-:3])=[O:2].[NH2:18][C:19]([CH3:24])=[CH:20][N+:21]([O-:23])=[O:22]>C(O)C>[CH3:16][C:15]1[NH:18][C:19]([CH3:24])=[C:20]([N+:21]([O-:23])=[O:22])[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=2)[C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 54296870HCID 54296870, compoundHCID 714047121-Nitroprop-1-en-2-amine

Product 1

HCID 131211851,4-Dihydro-2,6-dimethyl-3,5-dinitro-4-(3-nitrophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

23.6 g (0.1 mol) of 2-nitro-1-(3nitrophenyl)-but-1-ene-3-one and 10.2 g (0.1 mol) of 2-amino-1-nitro-prop-1-ene in 150 ml of ethanol were heated under reflux for 12 hours. After the mixture had cooled, the solvent was distilled off in vacuo, and the oily residue was taken up in chloroform, and was chromatographed on a silica gel column, using chloroform with the addition of methanol. The product formed yellow crystals of melting point 237°-240° C. (decomposition) in isopropanol.

Workup

  1. temperatureunder reflux for 12 hours
  2. temperatureAfter the 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. customThe product formed yellow crystals of melting point 237°-240° C. (decomposition) in isopropanol

Sources & evidence

ORD record
ord-e39d3ab89ae744699da76c9bfb4b04f5
Source dataset
uspto-grants-1985_07
Patent number
US04532248

Reaction notes

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