Aniline → HCID 20254854, compound

HRID 637984Notes

Reaction equation

HRID 637984 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][NH:10][C:3]=12.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[NH:11]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][NH:10][C:3]=12)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 137471767-Chloro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 20254854HCID 20254854, compoundYield 55%

Procedure

A solution of 7-chloro-1H-pyrazolo[4,3-b]pyridine (215 mg, 1.4 mmol) in aniline (1.3 ml) was heated under reflux under nitrogen for 16 h. The mixture was cooled, and the white solid which separated was collected, washed with 60°-80° petrol and water, then dried. The solid was then dissolved in 60% aqueous methanol (25 ml). The solution was filtered, adjusted to pH9 with 10% sodium carbonate solution, and on cooling the product crystallised, to give the title compound as needles (161 mg, 55%), m.p. 222°-224° C.

Workup

  1. temperatureunder reflux under nitrogen for 16 h
  2. temperatureThe mixture was cooled
  3. customthe white solid which separated
  4. customwas collected
  5. washwashed with 60°-80° petrol and water
  6. customdried
  7. dissolutionThe solid was then dissolved in 60% aqueous methanol (25 ml)
  8. filtrationThe solution was filtered
  9. temperatureon cooling the product
  10. customcrystallised

Sources & evidence

ORD record
ord-fae5c766a10048b49b0863030038c046
Source dataset
uspto-grants-1985_12
Patent number
US04559348

Reaction notes

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