Phenylhydrazine → 7-methoxy-1-phenyl-1H-pyrazolo[3,4-b]quinolin-3-amine

HRID 2073777Notes

Reaction equation

HRID 2073777 reaction equation
[H-].[Na+].[C:3]1([NH:9][NH2:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:12]1[C:21]([C:22]#[N:23])=[CH:20][C:19]2[C:14](=[CH:15][C:16]([O:24][CH3:25])=[CH:17][CH:18]=2)[N:13]=1>CN(C)C=O>[CH3:25][O:24][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[C:21]3[C:22]([NH2:23])=[N:10][N:9]([C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[C:12]3=[N:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 24758Sodium hydride2×HCID 7782502-Chloro-7-methoxyquinoline-3-carbonitrile

Product 1

HCID 148224757-methoxy-1-phenyl-1H-pyrazolo[3,4-b]quinolin-3-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 4.8 g sodium hydride (60%) in 200 ml dimethylformamide at 0° C. was added a solution of 9.9 ml phenylhydrazine in 250 ml dimethylformamide over a 15 min period. The mixture was stirred and allowed to warm to room temperature for 1 hour. 2-Chloro-7-methoxy-3-quinolinecarbonitrile (Example 3c) (19.68 g) was then added in portions. The reaction mixture was stirred overnight at room temperature, and then heated on a steam bath for two hours. Since starting material was still present, additional sodium hydride (3.2 g) was added and heating continued until thin layer chromatography indicated that no starting material remained. The mixture was quenched in saturated ammonium chloride solution and the mixture worked up in ethyl acetate solution. The crude product was purified by chromatography and recrystallized from ethyl acetate to give 2.3 g 7-methoxy-1-phenyl-1H-pyrazolo[3,4-b]quinolin-3-amine, brown solid, m.p. 159°-160° C.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. temperatureheated on a steam bath for two hours
  3. temperatureheating
  4. customThe mixture was quenched in saturated ammonium chloride solution
  5. customThe crude product was purified by chromatography
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-55400267dd3244d598e0fc70522b4253
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Reaction notes

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