Nitric Acid → HCID 19791105, compound

HRID 1655201Notes

Reaction equation

HRID 1655201 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:29])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH3:28])[CH2:23][CH2:22]1.[N+:30]([O-])([OH:32])=[O:31].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][CH2:11][CH2:12][NH:13][C:14](=[O:29])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH2:26]1)[N+:30]([O-:32])=[O:31]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 19791106HCID 19791106, compound

Product 1

HCID 19791105HCID 19791105, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.45 g of N-(11-hydroxy-1-undecanyl)-2-(4-ethyl-1-piperazinyl)nicotinamide were suspended in 100 ml of acetonitrile and to the suspension was added dropwise under ice-cooling a mixed solution of 2.0 ml of fuming nitric acid and 5.2 ml of acetic anhydride and stirred for 5 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. The concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1) to give 2.52 g (42%) of the title compound.

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
  6. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-10dbfd0f21ab45b7a91aa8d7188ed395
Source dataset
uspto-grants-1993_10
Patent number
US05250526

Reaction notes

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