2-Propanone, 1-nitro- → HCID 54296870, compound

HRID 1110345Notes

Reaction equation

HRID 1110345 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[CH:7]=NCCCC)([O-:3])=[O:2].[N+:16]([CH2:19][C:20](=[O:22])[CH3:21])([O-:18])=[O:17]>C(OC(=O)C)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:19]([N+:16]([O-:18])=[O:17])[C:20](=[O:22])[CH3:21])[CH:13]=[CH:14][CH:15]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 662962-Propanone, 1-nitro-HCID 14971160(E)-N-Butyl-1-(3-nitrophenyl)methanimine

Product 1

HCID 54296870HCID 54296870, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 28.6 g (0.39 mole) of the butanamine in 75 mL of acetic anhydride was added 15 g of 1-nitro-2-propanone. A white precipitate formed almost at once. The mixture was warmed gently until the solid dissolved, cooled, stirred for five hours, carefully poured onto water and extracted with ether. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. After storage at 0° C. overnight, the residue had crystallized. Recrystallization of the resulting solid from dibutyl ether gave 9.3 g of 4-(3-nitrophenyl)-3-nitro-3-buten-2-one, 1H NMR 8.4 (m, 2H), 7.7 (m, 2H), 7.5 (s, 1H), 2.5 (s, 3H).

Workup

  1. customA white precipitate formed almost at once
  2. temperatureThe mixture was warmed gently until the solid
  3. dissolutiondissolved
  4. temperaturecooled
  5. additioncarefully poured onto water
  6. extractionextracted with ether
  7. customThe organic layer was separated
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent removed under reduced pressure
  11. customAfter storage at 0° C. overnight, the residue had crystallized
  12. customRecrystallization of the resulting solid from dibutyl ether

Sources & evidence

ORD record
ord-c16a7a3e194648138e26583ea2eb4028
Source dataset
uspto-grants-1990_12
Patent number
US04975437

Reaction notes

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