Hydrochloric Acid → 2-Methyl-3-nitropyridine

HRID 1601142Notes

Reaction equation

HRID 1601142 reaction equation
C(OC(=O)[CH:5]([C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1)C(OCC)=O)C.Cl>O>[CH3:5][C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13147345Diethyl (3-nitropyridin-2-yl)propanedioate

Product 1

HCID 3293602-Methyl-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 43 g (115 mmol) of diethyl(3-nitropyridin-2-yl)malonate (purity approximately 75%; Example 3.a) and 150 ml of 18% strength hydrochloric acid was stirred for 3 hours at 100 ° C. After the mixture had cooled to room temperature (approximately 25° C.), it was diluted with water and extracted using tert-butyl methyl ether. The aqueous phase was evaporated under reduced pressure, and the resulting crystalline residue was taken up in (aqueous) Na2CO3 solution. The Na2CO3 solution was extracted repeatedly using methylene chloride. The organic phases were combined, washed and dried, and the solvent was removed under reduced pressure. This gave 10 g (79%) of the title compound as a yellow oil.

Workup

  1. temperatureAfter the mixture had cooled to room temperature (approximately 25° C.), it
  2. extractionextracted
  3. customThe aqueous phase was evaporated under reduced pressure
  4. extractionThe Na2CO3 solution was extracted repeatedly using methylene chloride
  5. washwashed
  6. customdried
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8c0332871eb24874b2e1396bae93e085
Source dataset
uspto-grants-1999_11
Patent number
US05977146

Reaction notes

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