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

HRID 1615937Notes

Reaction equation

HRID 1615937 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 in the course of cooling. Water (380 ml) was added to the yellow crystals, and the mixture was stirred 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 in the course
  4. temperatureof cooling
  5. additionWater (380 ml) was added to the yellow crystals
  6. stirringthe mixture was stirred 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-dcb201ed2c6d4f6c9f754addaa8860a3
Source dataset
uspto-grants-2014_07
Patent number
US08765769B2

Reaction notes

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