Nitric Acid → HCID 10086103, compound

HRID 728117Notes

Reaction equation

HRID 728117 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[N+:22]([O-])([OH:24])=[O:23]>>[CH3:1][C:2]1[C:3]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[C:14]([N+:22]([O-:24])=[O:23])[CH:15]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 10400088HCID 10400088, compound

Product 1

HCID 10086103HCID 10086103, compound

Procedure

To a solution of fuming nitric acid (d.l.50) (80 ml) was portionwise added 3-methyl-2-[2-(4-acetamidophenyl)ethyl]pyridine (16.2 g) at -15° to 15° C. and the mixture was stirred at the same condition for 30 minutes. The resultant solution was poured into an ice-water and the solution was adjusted to pH 8.0 with 20% aqueous sodium hydroxide. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran, and the extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from a mixture of ethyl acetate and diethyl ether to give 3-methyl-2-[2-(4-acetamido-3-nitrophenyl)ethyl]pyridine (16.9 g).

Workup

  1. customat -15° to 15° C.
  2. extractionThe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  3. washthe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was recrystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-c1cc96c97b0c4f91839741a515d31570
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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