Nitric Acid → HCID 15678828, compound

HRID 982144Notes

Reaction equation

HRID 982144 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[N:8][CH:7]=1.[N+:20]([O-])([OH:22])=[O:21].C(=O)([O-])O.[Na+]>C(Cl)Cl>[O:1]([CH2:2][CH2:3][NH:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]2)=[N:8][CH:7]=1)[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 15678822HCID 15678822, compound

Product 1

HCID 15678828HCID 15678828, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 11.00 g of the compound (obtained in Example 1) in 20 ml of methylene chloride was added dropwise 5 ml of fuming nitric acid while stirring below 0° C. The stirring was continued for 2 hours. The reaction mixture was poured into an aqueous sodium hydrogen carbonate solution and extracted with methylene chloride. The extract was washed twice with water and once with a saturated aqueous saline solution, dried over anhydrous magnesium sulfate and concentrated to afford N-(2-nitroxyethyl)-6-(4-methyl-1-piperazinyl)nicotinamide. The product was dissolved in ethanol and to the solution was added under ice-cooling hydrogen chloride-saturated ethanol. The hydrochloride thus formed was recrystallized from ethanol to give 0.54 g of N-(2-nitroxyethyl)-6-(4-methyl-1piperazinyl)nicotinamide dihydrochloride (yield 34%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed twice with water and once with a saturated aqueous saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c11e179c34b84141b4e0589ba22e30e8
Source dataset
uspto-grants-1991_02
Patent number
US04994456

Reaction notes

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