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

HRID 1095358ノート

反応式

HRID 1095358 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-90a4aed787394a7687507d586b04b35c
出典データセット
uspto-grants-2012_03
特許番号
US08138173B2

反応ノート

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