Acetylacetone → 2-Amino-4,6-dimethyl-3-nitropyridine

HRID 1440300Notes

Reaction equation

HRID 1440300 reaction equation
[NH2:1][C:2]([NH2:7])=[CH:3][N+:4]([O-:6])=[O:5].[C:8]([CH2:11][C:12](=O)[CH3:13])(=O)[CH3:9]>COCCO>[NH2:1][C:2]1[C:3]([N+:4]([O-:6])=[O:5])=[C:12]([CH3:13])[CH:11]=[C:8]([CH3:9])[N:7]=1

Participants

4

Reactant 2

HCID 31261AcetylacetoneHCID 189193Ethene-1,1-diamine, 2-nitro-

Product 1

HCID 2984722-Amino-4,6-dimethyl-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

3 g (29.1 mmol) of 1,1-diamino-2-nitroethene and 11.6 (17.4 mmol) of acetylacetone were maintained at reflux in 40 ml of 2methoxyethanol for 6 hours. The solvent was then removed in vacuo, the residue was slurried in 20 ml of iced water and filtered. Drying of the filter cake gave 4.52 (93 percent) of the title product. The product had a melting point of 165° C. Other data concerning the product was:

Workup

  1. customThe solvent was then removed in vacuo
  2. filtrationfiltered
  3. customDrying of the filter cake

Sources & evidence

ORD record
ord-14ab1a59360745aaa92bff15b8b0be17
Source dataset
uspto-grants-1996_03
Patent number
US05498715

Reaction notes

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