Ammonium Hydroxide → HCID 11842676, compound

HRID 1095342Notes

Reaction equation

HRID 1095342 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][CH2:17][CH3:18])[N:4]=[C:5]2[C:14]=1[C:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:7]=[C:6]2O.[OH-].[NH4+].P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:6]1[C:5]2=[N:4][N:3]([CH2:16][CH2:17][CH3:18])[C:2]([CH3:1])=[C:14]2[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:7]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 178456619HCID 178456619, compound

Product 1

HCID 11842676HCID 11842676, compound

Procedure

A solution of 1-methyl-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ol (5.11 g, 21.2 mmol) in phosphorus oxychloride (50 mL) was heated at reflux for 30 minutes, allowed to cool to room temperature, and stirred for two days. The reaction mixture was poured into ice water (500 mL) with stirring, and concentrated ammonium hydroxide (169 mL) and ice were added. A solid was present and was isolated by filtration, washed with water, and purified by automated flash chromatography (eluting with 5% to 25% CMA in chloroform). The resulting orange solid (5.5 g) was recrystallized from acetonitrile (25 mL). The crystals were washed with acetonitrile and dried for five hours to provide 3.85 g of 4-chloro-1-methyl-2-propyl-2H-pyrazolo[3,4-c]quinoline as a white solid, mp 145-147° C. Anal. Calcd for C14H14N3Cl: C, 64.74; H, 5.43; N, 16.18. Found: C, 64.50; H, 5.64; N, 16.20.

Workup

  1. temperatureat reflux for 30 minutes
  2. stirringwith stirring
  3. customwas isolated by filtration
  4. washwashed with water
  5. custompurified by automated flash chromatography (eluting with 5% to 25% CMA in chloroform)
  6. customThe resulting orange solid (5.5 g) was recrystallized from acetonitrile (25 mL)
  7. washThe crystals were washed with acetonitrile
  8. customdried for five hours

Sources & evidence

ORD record
ord-7e80cffd913b4a949e30f97f96cb729f
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

Loading…