1-Methylpyrrolidine → HCID 14822500, compound

HRID 2073784Notes

Reaction equation

HRID 2073784 reaction equation
Br[C:2]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=3)[N:4]([CH3:17])[N:3]=1.[CH3:18][N:19]1CCCC1>>[CH3:16][O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[N:6]=[C:5]1[N:4]([CH3:17])[N:3]=[C:2]([C:18]#[N:19])[C:14]1=[CH:13]2

Participants

3

Reactant 2

HCID 84541-MethylpyrrolidineHCID 14822499HCID 14822499, compound

Product 1

HCID 14822500HCID 14822500, compound

Procedure

A mixture of 32.0 g 3-bromo-6-methoxy-1-methyl-1H-pyrazolo[3,4-b]quinoline (Example 32) and 20.2 g cuprous bromide in 220 ml N-methylpyrrolidine was stirred and heated at reflux for 3 hours. The reaction mixture was poured into ice-water, and the solid product was collected by filtration. The latter product was treated with dilute aqueous sodium cyanide and purified by extraction with ethyl acetate and chromatography to give 4.5 g 6-methoxy-1-methyl-1H-pyrazolo[3,4-b]quinoline-3-carbonitrile, bright-yellow solid, m.p. 190°-191° C., when recrystallized from methanol.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. filtrationthe solid product was collected by filtration
  4. additionThe latter product was treated with dilute aqueous sodium cyanide
  5. custompurified by extraction with ethyl acetate and chromatography

Sources & evidence

ORD record
ord-12eff6c8e1124a42a7a732ca3db0d05c
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Reaction notes

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