Carbon Dioxide → 2-(Chloromethyl)-3-methyl-4-nitropyridine 1-oxide

HRID 979842Notes

Reaction equation

HRID 979842 reaction equation
S(=O)(=O)(O)O.C(=O)=O.[N+:9]([O-:12])(O)=[O:10].[Cl:13][CH2:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N+:16]=1[O-:22]>C(Cl)Cl>[Cl:13][CH2:14][C:15]1[C:20]([CH3:21])=[C:19]([N+:9]([O-:12])=[O:10])[CH:18]=[CH:17][N+:16]=1[O-:22]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 221514452-Chloromethyl-3-methylpyridine 1-oxide

Product 1

HCID 17146902-(Chloromethyl)-3-methyl-4-nitropyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

300 ml of concentrated sulfuric acid was added slowly while cooling with dry ice to 230 ml of concentrated nitric acid (68%:d=1.41), while the temperature of the mixture was not allowed to exceed 5°. A solution of 38.7 g of 2-chloromethyl-3-methylpyridine 1-oxide was added thereto and the mixture was stirred at 80° for 2 hours. The reaction mixture was poured into a mixture of ice and methylene chloride, the aqueous phase was washed several times with methylene chloride and the methylene chloride solution was extracted with 10% sodium bicarbonate solution. The organic phase was dried with sodium sulfate and concentrated. The residue is recrystallized from ethyl acetate, there being obtained 2-chloromethyl-3-methyl-4-nitropyridine 1-oxide. The product has a melting point of 126°-129°.

Workup

  1. customto exceed 5°
  2. washthe aqueous phase was washed several times with methylene chloride
  3. extractionthe methylene chloride solution was extracted with 10% sodium bicarbonate solution
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is recrystallized from ethyl acetate, there

Sources & evidence

ORD record
ord-77778a1a425e4ddba99bb070a246c2b8
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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