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

HRID 1095358노트

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HRID 1095358 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-90a4aed787394a7687507d586b04b35c
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138173B2

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