Water → HCID 178509230, compound

HRID 1529155Notes

Reaction equation

HRID 1529155 reaction equation
Cl[C:2]1[N:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5].O.[NH2:12][NH2:13].O>C(O)CO>[F:10][C:7]1[CH:6]=[C:3]2[C:4]([NH2:5])=[N:13][NH:12][C:2]2=[N:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 231108512-Chloro-5-fluoropyridine-3-carbonitrile

Product 1

HCID 178509230HCID 178509230, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A suspension of 38.5 g (245.93 mmol) of 2-chloro-5-fluoronicotinonitrile was initially charged in 1,2-ethanediol (380 ml), and hydrazine hydrate (119.6 ml) was then added. With stirring, the mixture was heated at reflux for 4 h. Cooling resulted in the precipitation of a solid, which was admixed with water (380 ml) and extracted by stirring at RT for 10 min. The suspension was then filtered with suction through a frit, and the filter cake was washed with water (200 ml) and with THF at −10° C. (200 ml). The solid was dried under high vacuum over phosphorus pentoxide.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 h
  3. temperatureCooling
  4. customresulted in the precipitation of a solid, which
  5. extractionextracted
  6. stirringby stirring at RT for 10 min
  7. filtrationThe suspension was then filtered with suction through a frit
  8. washthe filter cake was washed with water (200 ml) and with THF at −10° C. (200 ml)
  9. dry with materialThe solid was dried under high vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-effdd34ab81441f29f8ec6ca0489bf0f
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

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