Ammonium Hydroxide → HCID 11842676, compound

HRID 549231Notes

Reaction equation

HRID 549231 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.

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-ee3953045de747cdb07ea38e8ddfe2ef
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

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