Hydrazine hydrate (1:1) → HCID 178509230, compound

HRID 1777799Notes

Reaction equation

HRID 1777799 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]>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

4

Reactant 2

HCID 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, 2.459 mol) was then added. The mixture was heated under reflux with stirring for 4 h. The product precipitated on cooling. Water (380 ml) was added to the yellow crystals, and the mixture was subjected to extractive stirring at RT for 10 min. The suspension was then filtered with suction over a frit, and the filter product was washed with water (200 ml) and with −10° C. cold THF (200 ml). The residue was dried under high vacuum over phosphorus pentoxide.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customThe product precipitated
  4. temperatureon cooling
  5. additionWater (380 ml) was added to the yellow crystals
  6. stirringto extractive stirring at RT for 10 min
  7. filtrationThe suspension was then filtered with suction over a frit
  8. washthe filter product was washed with water (200 ml) and with −10° C. cold THF (200 ml)
  9. dry with materialThe residue was dried under high vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-7b990ebe8ea04a6683502eecd3141620
Source dataset
uspto-grants-2016_02
Patent number
US09266885B2

Reaction notes

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