Nitric Acid → HCID 13419572, compound

HRID 1655238Notes

Reaction equation

HRID 1655238 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[N+:6]([O-:8])[CH:7]=1.OS(O)(=O)=O.O=S(=O)=O.[N+:19]([O-])([OH:21])=[O:20].C(=O)([O-])[O-].[NH4+].[NH4+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([N+:19]([O-:21])=[O:20])=[CH:4][C:5]([CH3:9])=[N+:6]([O-:8])[CH:7]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 24681Fuming sulfuric acidHCID 517111Ammonium CarbonateHCID 817170HCID 817170, compound

Product 1

HCID 13419572HCID 13419572, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 5-chloro-2-methylpyridine-N-oxide (9.46 g) in concentrated sulphuric acid (30 ml), a nitration mixture consisting of 30% oleum (28 ml) and fuming nitric acid (47 ml), was added dropwise at 5°-8° over 20 minutes. The reaction mixture was allowed to stand for one hour at room temperature and then heated for 2 hours on a steam bath After allowing to cool the solution was poured onto ice and carefully neutralised with ammonium carbonate, added in portions. The solid was extracted into chloroform, dried, stripped and triturated with petrol to give 5-chloro-4-nitro-2-methylpyridine-N-oxide, (9.83 g), m.p.120°-122°

Workup

  1. additionwas added dropwise at 5°-8° over 20 minutes
  2. temperatureheated for 2 hours on a steam bath
  3. temperatureto cool the solution
  4. additionwas poured onto ice
  5. additionadded in portions
  6. extractionThe solid was extracted into chloroform
  7. customdried
  8. customtriturated with petrol

Sources & evidence

ORD record
ord-3c3f750c0f5c4fdf88dac7cfc31a0029
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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