HCID 14822471, compound → HCID 178481929, compound

HRID 2073778Notes

Reaction equation

HRID 2073778 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]3[C:15]([NH2:16])=[N:14][N:13]([CH3:17])[C:9]3=[N:10]2)=[CH:5][CH:4]=1>Br>[NH2:16][C:15]1[C:8]2[C:9](=[N:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[C:3]([OH:2])[CH:12]=3)[N:13]([CH3:17])[N:14]=1

Participants

3

Reactant 1

HCID 14822471HCID 14822471, compound

Product 1

HCID 178481929HCID 178481929, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 20.9 g 7-methoxy-1-methyl-1H-pyrazolo[3,4-b]quinolin-3-amine (Example 7) and 420 ml 48% aqueous hydrobromic acid was stirred at reflux for 21 hours. The reaction mixture was quenched in ice-water and neutralized to pH 7.0 with ammonium hydroxide. The resulting yellow solid was collected by filtration, washed with water and recrystallized from 1100 ml absolute ethanol to provide 12.4 g (63%) 3-amino-1-methyl-1H-pyrazolo[3,4-b]quinolin-7-ol, orange-yellow solid, m.p. 288°-290° C. (decompn).

Workup

  1. temperatureat reflux for 21 hours
  2. customThe reaction mixture was quenched in ice-water and neutralized to pH 7.0 with ammonium hydroxide
  3. filtrationThe resulting yellow solid was collected by filtration
  4. washwashed with water
  5. customrecrystallized from 1100 ml absolute ethanol

Sources & evidence

ORD record
ord-31156b2ca00142c6aece661f6bc93b7b
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Reaction notes

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