Dimethylamine → (E)-3-(2-(Dimethylamino)vinyl)-4-nitropyridine 1-oxide

HRID 2201790Notes

Reaction equation

HRID 2201790 reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].CNC.O.[CH3:16][N:17]([CH3:20])[CH:18]=O>>[CH3:16][N:17]([CH3:20])/[CH:18]=[CH:1]/[C:2]1[CH:3]=[N+:4]([O-:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 6228Dimethylformamide2×HCID 70633Pyridine, 3-methyl-4-nitro-, 1-oxide

Product 1

HCID 11344817(E)-3-(2-(Dimethylamino)vinyl)-4-nitropyridine 1-oxideYield 50%

Conditions

Temperature
90 °C

Procedure

To the stirred solution of 3-methyl-4-nitropyridine 1-oxide (600 mg, 3.8 mmol, Step b) in dimethylformamide was added dimethylformamide and dimethylamine (1.14 mL, 8.5 mmol) drop wise at room temperature. After complete addition, the reaction mixture was stirred at 90° C. for 15 hours. The reaction mixture was poured on cold water and the precipitated solid was filtered, washed with water and dried to get (E)-N,N-dimethyl-2-(4-nitro-1-oxidopyridin-3-yl)ethenamine (470 mg, 50%).

Workup

  1. additionAfter complete addition
  2. filtrationthe precipitated solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d434a110303245b1b55d884c5c5a04e5
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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