Nitric Acid → HCID 19791097, compound

HRID 1655200Notes

Reaction equation

HRID 1655200 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[N:16][CH:15]=1.C(=O)([O-])O.[Na+].[N+:33]([O-])([OH:35])=[O:34]>>[O:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:27])[C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]2)=[N:16][CH:15]=1)[N+:33]([O-:35])=[O:34]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 19791104HCID 19791104, compound

Product 1

HCID 19791097HCID 19791097, compoundYield 42%

Procedure

6.00 g of N-(10-hydroxy-1-decanyl)-6-(4-methyl-1-piperazinyl)nicotinamide were added under ice-cooling to 20 ml of fuming nitric acid and the mixture was stirred below -5° C. for 4 hrs. This mixture was poured into an aqueous sodium hydrogencarbonate solution, extracted with methylene chloride, washed with eater and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1) and recrystallized from acetone-hexane to give 2.80 g (42%) of the title compound. m.p.62°-64° C.

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with eater
  3. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1)
  6. customrecrystallized from acetone-hexane

Sources & evidence

ORD record
ord-6c02b11bc3404b40bda132ad1fb2b407
Source dataset
uspto-grants-1993_10
Patent number
US05250526

Reaction notes

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