Hydrochloric Acid → 5-Nitro-2-(2-cyanoethyl)-3-methylpyridine

HRID 34926

Reaction equation

HRID 34926 reaction equation
[CH3:1][C:2]1[C:3]([C:11](C(OCC)=O)(C(OCC)=O)[CH2:12][C:13]#[N:14])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[OH-].[Na+].Cl>CO>[N+:8]([C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([CH2:11][CH2:12][C:13]#[N:14])=[N:4][CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 198517963-(3-Methyl-5-nitropyrid-2-yl)-3,3-bis(carbethoxy)propionitrile

Product 1

HCID 198517775-Nitro-2-(2-cyanoethyl)-3-methylpyridineYield 61.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(3-Methyl-5-nitropyrid-2-yl)-3,3-bis(carbethoxy)propionitrile (29.8 g) was dissolved in methanol (1120 ml), molar sodium hydroxide solution (355 ml) was added, the reaction was cooled from 28° C. to room temperature and stirred for 55 minutes. The pH was lowered to 4 by the addition of concentrated hydrochloric acid, the reaction was stirred for 2.75 hr., the pH was then raised to 7 and the methanol was distilled off. The aqueous phase was extracted with chloroform, extracts were dried, filtered and concentrated. The residue was crystallised from chloroform/petroleum ether 40°-60° C. The crude product was treated with charcoal in ethanol and recrystallised from ethanol to give the title compound 10.44 g, m.p. 73°-74° C.

Workup

  1. temperaturethe reaction was cooled from 28° C. to room temperature
  2. stirringthe reaction was stirred for 2.75 hr
  3. temperature, the pH was then raised to 7
  4. distillationthe methanol was distilled off
  5. extractionThe aqueous phase was extracted with chloroform, extracts
  6. customwere dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was crystallised from chloroform/petroleum ether 40°-60° C
  10. additionThe crude product was treated with charcoal in ethanol
  11. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-53d7ad8220734ff5868589de7ff6ea4e
Source dataset
uspto-grants-1988_08
Patent number
US04764519

Linked notes

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