Nitric Acid → HCID 10901874, compound

HRID 368983Notes

Reaction equation

HRID 368983 reaction equation
[C:1]([C:9]1[C:10]([Cl:16])=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([O-])([OH:19])=[O:18].[OH-].[Na+]>S(=O)(=O)(O)O>[Cl:16][C:10]1[C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[C:6]([N+:17]([O-:19])=[O:18])[CH:7]=2)=[CH:14][CH:13]=[C:12]([CH3:15])[N:11]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 10955416HCID 10955416, compound

Product 1

HCID 10901874HCID 10901874, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

3-Benzoyl-2-chloro-6-methylpyridine (3.00 g, 12.9 mmol) dissolved in 40 ml of concentrated sulfuric acid was cooled to 5° C. or lower, 1.0 ml of fuming nitric acid was slowly added dropwise thereto, followed by stirring for 30 minutes. The reaction solution was poured into ice water, neutralized with sodium hydroxide aqueous solution and then extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the solvent was evaporated under a reduced pressure and the resulting residue was recrystallized from ethyl aretate-diisopropyl ether to give 1.81 g (51%) of 2-chloro-6-methyl-3-(3-nitrobenzoyl)pyridine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing magnesium sulfate
  5. filtrationby filtration
  6. customthe solvent was evaporated under a reduced pressure
  7. customthe resulting residue was recrystallized from ethyl aretate-diisopropyl ether

Sources & evidence

ORD record
ord-14257d5354b14f82abc606c72e255ffe
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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