Nitric Acid → HCID 19791107, compound

HRID 1655199Notes

Reaction equation

HRID 1655199 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:26])[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)=[N:15][CH:14]=1.[N+:27]([O-])([OH:29])=[O:28].C(OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C>[O:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:26])[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)=[N:15][CH:14]=1)[N+:27]([O-:29])=[O:28]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 19791109HCID 19791109, compound

Product 1

HCID 19791107HCID 19791107, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.67 g of N-(9-hydroxy-1-nonyl)-6-(4-methyl-1-piperazinyl)nicotinamide were suspended in 40 ml of acetonitrile and to the suspension was added dropwise under ice-cooling a mixed solution of 0.8 ml of fuming nitric acid and 1.9 ml of acetic anhydride and stirred for 6 hrs. This reaction mixture was poured into an aqueous sodium hydrogencarbonate solution, extracted with methylene chloride, washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated to give 1.30 g (69%) of the title compound. m.p. 90°-92° C.

Workup

  1. additionwas added dropwise under ice-
  2. extractionextracted with methylene chloride
  3. washwashed with water
  4. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f1a12048ba746ee9e735ef71411e9d3
Source dataset
uspto-grants-1993_10
Patent number
US05250526

Reaction notes

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