Dimethylformamide → 4-chloro-1-ethyl-2-phenyl-2H-pyrazolo[3,4-c]quinoline

HRID 1095358Notes

Reaction equation

HRID 1095358 reaction equation
S(Cl)(Cl)=O.CN(C=O)C.[CH2:10]([C:12]1[N:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:14]=[C:15]2[C:24]=1[C:23]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:17][C:16]2=O)[CH3:11].[Cl:32]CCl>C(#N)C>[Cl:32][C:16]1[C:15]2=[N:14][N:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:12]([CH2:10][CH3:11])=[C:24]2[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 574462221-ethyl-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one

Product 1

HCID 574462234-chloro-1-ethyl-2-phenyl-2H-pyrazolo[3,4-c]quinoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (4 mL) and DMF (4 mL) were combined and added dropwise to a mixture of 1-ethyl-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one (1.29 g, 4.40 mmol) and dichloromethane (80 mL) at 0° C. The resulting suspension was stirred 5 minutes at 0° C. before warming to ambient temperature and stirring 50 minutes. The suspension was concentrated under reduced pressure to afford an oily solid that was stirred in acetonitrile and filtered to obtain 450 mg of 4-chloro-1-ethyl-2-phenyl-2H-pyrazolo[3,4-c]quinoline as white crystals, mp 207-209° C. MS (APCI) m/z 308 (M+H)+; Anal. calcd for C18H14ClN3: C, 70.24; H, 4.58; N, 13.65. Found: C, 69.94; H, 4.48; N, 13.54

Workup

  1. temperaturebefore warming to ambient temperature
  2. stirringstirring 50 minutes
  3. concentrationThe suspension was concentrated under reduced pressure
  4. customto afford an oily solid
  5. filtrationfiltered

Sources & evidence

ORD record
ord-90a4aed787394a7687507d586b04b35c
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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