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

HRID 1505449Notes

Reaction equation

HRID 1505449 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) was then added. With stirring, the mixture was heated at reflux for 4 h. On cooling, the product precipitated out. Water (380 ml) was added to the crystals, and the mixture was stirred at RT for 10 min. The suspension was then filtered off with suction through a frit and washed with water (200 ml) and with −10° C.-cold THF (200 ml). Drying under high vacuum over phosphorus pentoxide.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 h
  3. temperatureOn cooling
  4. customthe product precipitated out
  5. additionWater (380 ml) was added to the crystals
  6. stirringthe mixture was stirred at RT for 10 min
  7. filtrationThe suspension was then filtered off with suction through a frit
  8. washwashed with water (200 ml) and with −10° C.-cold THF (200 ml)
  9. dry with materialDrying under high vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-9e619284fc9549f8bec11b3da77a1904
Source dataset
uspto-grants-2015_12
Patent number
US09216978B2

Reaction notes

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