4-Aminophenol → 7-(4-Hydroxyanilino)-5-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 482897Notes

Reaction equation

HRID 482897 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.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1>C1(C)C(C)=CC=CC=1>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]3[CH:9]=[N:10][NH:11][C:3]=23)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 116798717-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 1359993657-(4-Hydroxyanilino)-5-methyl-1H-pyrazolo[4,3-b]pyridineYield 54.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

7-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (0.5 g, 3 mmol) and 4-aminophenol (0.65 g, 6 mmol) in dry xylene (5 ml) were heated under reflux under nitrogen for 7 h. The resulting solid was collected and washed with water and ethyl acetate, then crystallised from methanol/ethyl acetate to give the hydrochloride salt of the required product (393 mg, 47%), m.p. 308°-310° C. (dec.).

Workup

  1. temperatureunder reflux under nitrogen for 7 h
  2. customThe resulting solid was collected
  3. washwashed with water and ethyl acetate
  4. customcrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-e1491710df6b491fa5a00f3d78b6a547
Source dataset
uspto-grants-1986_03
Patent number
US04576952

Reaction notes

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