Hydrochloric Acid → 7-Benzylamino-5-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 637983Notes

Reaction equation

HRID 637983 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]=12.Cl.C(=O)([O-])[O-].[Na+].[Na+].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([NH:26][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]=12)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 10340Sodium CarbonateHCID 116798717-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 202548677-Benzylamino-5-methyl-1H-pyrazolo[4,3-b]pyridine

Procedure

7-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (1 g) and benzylamine (30 ml) were heated under reflux for 6 h. The benzylamine was removed in vacuo to yield an oily solid which was digested with 20% hydrochloric acid. The digest was basified with 10% sodium carbonate solution to yield two phases. The solid in the aqueous phase was filtered off to yield the product (0.71 g). The remaining oily phase was extracted with boiling chloroform (3×20 ml) and the extract dried (MgSO4) and evaporated to yield a second crop of product (0.54 g). The combined solids (1.25 g, 91%) were recrystallised from ethanol/petroleum ether to yield the 7-benzylamino-compound as white crystals m.p. 205°-206°.

Workup

  1. temperatureunder reflux for 6 h
  2. customThe benzylamine was removed in vacuo
  3. customto yield an oily solid which
  4. customto yield two phases
  5. filtrationThe solid in the aqueous phase was filtered off

Sources & evidence

ORD record
ord-c3f542636fcb434aa952b6bc152e2cf4
Source dataset
uspto-grants-1985_12
Patent number
US04559348

Reaction notes

Loading…