Dimethylformamide → HCID 10443354, compound

HRID 1720255Notes

Reaction equation

HRID 1720255 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[CH:14]=[N:13][NH:12][C:10]3=2)[N:5]=[C:4]([CH3:15])[CH:3]=1.P(Cl)(Cl)([Cl:18])=O.CN(C)C=O.[OH-].[Na+]>O>[Cl:18][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[CH:14]=[N:13][NH:12][C:10]3=2)[N:5]=[C:4]([CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178428803HCID 178428803, compound

Product 1

HCID 10443354HCID 10443354, compoundYield 92,692.898%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 9-hydroxy-7-methyl-1H-pyrazolo[3,4-f]quinoline (8.00 g, 0.04 mmol) in phosphorus oxychloride (61.6 g, 0.40 mol) was added slowly N,N-dimethylformamide (40 ml). After the addition was complete, the reaction mixture was warmed to 80° C. for 1 hour and then allowed to cool to room temperature. The reaction was poured onto ice and dissolved in water (2 L total volume) and neutralized to pH 7 with 20% sodium hydroxide (NaOH). The precipitate which formed upon neutralization was collected by filtration, washed with water and dried under vacuum to give 9-chloro-7-methyl-1H-pyrazolo[3,4-f]quinoline as a white solid (8.07 g, 92%).

Workup

  1. additionAfter the addition
  2. temperatureto cool to room temperature
  3. additionThe reaction was poured onto ice
  4. customThe precipitate which formed upon neutralization
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-dbd171e32d39420da883cea6c9363db1
Source dataset
uspto-grants-1996_04
Patent number
US05506235

Reaction notes

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