2-Nitropropane → 4-Methyl-4-nitro-1-phenyl-3-(pyridin-3-yl)pentan-1-one

HRID 1730158Notes

Reaction equation

HRID 1730158 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:2]=1.[N+:17]([CH:20]([CH3:22])[CH3:21])([O-:19])=[O:18].CC[O-].[Na+].[Na]>C(O)C>[CH3:21][C:20]([N+:17]([O-:19])=[O:18])([CH3:22])[CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 3982-NitropropaneHCID 219206HCID 219206, compoundHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 126213674-Methyl-4-nitro-1-phenyl-3-(pyridin-3-yl)pentan-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 51.8 g. of 3-(3-pyridyl)-acrylophenone and 44.2 g. of 2-nitropropane in 496 ml. of ethanol are heated at reflux with stirring in a nitrogen atmosphere. Then, a sodium ethylate solution manufactured from 2.54 g. of sodium and 49.6 ml. of ethanol is added dropwise within 1 hour. The reaction mixture is left standing for an additional half hour to react further and then evaporated under reduced pressure. The resulting residue is taken up in 1000 ml. of methylene chloride, washed three times with 300 ml. of water each time, dried over sodium sulfate, evaporated under reduced pressure and crystallized from methanol to yield 4-methyl-4-nitro-3-(3-pyridyl)-valerophenone with a melting point of 134°-135° C.

Workup

  1. temperatureat reflux
  2. waitThe reaction mixture is left
  3. customto react further
  4. customevaporated under reduced pressure
  5. washof methylene chloride, washed three times with 300 ml
  6. dry with materialof water each time, dried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customcrystallized from methanol

Sources & evidence

ORD record
ord-0c9aaeb310c64da4a36b0dffcef91c1c
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

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