Nitromethane → HCID 70374866, compound

HRID 329901Notes

Reaction equation

HRID 329901 reaction equation
[CH:1]([C:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]=1)=O.C(N)CCC.[N+:19]([CH3:22])([O-:21])=[O:20]>C1(C)C=CC=CC=1>[C:8]1([N:5]2[CH2:6][CH:7]=[C:3]([CH:1]=[CH:22][N+:19]([O-:21])=[O:20])[NH:4]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8007ButylamineHCID 19870269HCID 19870269, compound

Product 1

HCID 70374866HCID 70374866, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-formyl-1-phenyl-2-pyrazoline (3.48 g), n-butylamine (0.2 ml) and nitromethane (10 ml) was stirred at 100° C. for 1 hour, then was cooled to room temperature. The resultant dark red crystalline mass was dissolved in toluene and was eluted down a silica column with toluene. The major orange fraction was evaporated to dryness under reduced pressure and the residue was recrystallised from ethanol to give a 59% yield of dark red micro crystals (MP 150° C.).

Workup

  1. temperaturewas cooled to room temperature
  2. washwas eluted down a silica column with toluene
  3. customThe major orange fraction was evaporated to dryness under reduced pressure
  4. customthe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-9037742ff7da4e87b5505f4283a57094
Source dataset
uspto-grants-1990_01
Patent number
US04894186

Reaction notes

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