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

HRID 510027Notes

Reaction equation

HRID 510027 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 while stirring for 4 h. The product precipitated out in the course of cooling. Water (380 ml) was added to the yellow crystals, and extraction was effected by stirring at RT for 10 min. The suspension was then filtered with suction through a frit and washed through with water (200 ml) and with THF at −10° C. (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 out in the course
  4. temperatureof cooling
  5. additionWater (380 ml) was added to the yellow crystals, and extraction
  6. stirringby stirring at RT for 10 min
  7. filtrationThe suspension was then filtered with suction through a frit
  8. washwashed through with water (200 ml) and with THF at −10° C. (200 ml)
  9. dry with materialThe residue was dried under high vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-95c48b4bbeba4e2bb24d034a4279465a
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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