4-Aminophenol → HCID 136472793, compound

HRID 482898Notes

Reaction equation

HRID 482898 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][C:15]([OH:18])=[CH:14][CH:13]=1>C1(C)C(C)=CC=CC=1>[OH2:18].[OH:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[N:9][NH:10][C:3]=23)=[CH:13][CH:14]=1.[OH:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[N:9][NH:10][C:3]=23)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 137471767-Chloro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 136472793HCID 136472793, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 7-chloro-1H-pyrazolo[4,3-b]pyridine (0.50 g, 3.26 mmol) and 4-aminophenol (0.71 g, 6.52 mmol) in xylene (10 ml) was heated under reflux under nitrogen for 5 h. After cooling the reaction mixture, the solid was collected and washed well with ethyl acetate and water. The solid was then dissolved in warm aqueous methanol, and the solution was adjusted to pH 8 with saturated sodium bicarbonate solution. The product separated as needles, which were recrystallised from aqueous methanol to give the title compound (260 mg, 35%), mp 286°-296° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 5 h
  3. temperatureAfter cooling the reaction mixture
  4. customthe solid was collected
  5. washwashed well with ethyl acetate and water
  6. dissolutionThe solid was then dissolved in warm aqueous methanol
  7. customThe product separated as needles, which
  8. customwere recrystallised from aqueous methanol

Sources & evidence

ORD record
ord-704fa2c229a0478bbffa28b48a323274
Source dataset
uspto-grants-1986_03
Patent number
US04576952

Reaction notes

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