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Triethylamine → 6-Chloro-4-(4-fluorophenyl)-2-methyl-3-quinolinecarboxaldehyde

HRID 34295
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HRID 34295 반응식
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH3:18])[C:12]([CH2:19][OH:20])=[C:11]2[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1.C(N(CC)CC)C>ClCCl.CS(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH3:18])[C:12]([CH:19]=[O:20])=[C:11]2[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14229327HCID 14229327, 화합물

생성물 1

HCID 142293286-Chloro-4-(4-fluorophenyl)-2-methyl-3-quinolinecarboxaldehyde

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 6344Dichloromethane용매
3회

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온도
-78 °C

실험 절차

To a solution of oxalyl chloride (8.85 mL, 1.1 equivalents) in 150 mL of dry dichloromethane at -78° C. under nitrogen, was added dropwise a solution of dimethylsulfoxide (14.2 mL, 2.2 equivalents) in 125 mL of dichloromethane. After complete addition, the mixture was stirred for five minutes at -78° C. and then a solution of 6-chloro-4-(4-fluorophenyl)-2-methyl-3-quinolinemethanol (27.8 ) in 100 mL of dichloromethane and 50 mL of dimethylsulfoxide was added dropwise. This solution was stirred at -78° C. for one hour, after which triethylamine (64.1 mL, 5.0 equivalents) was added. The cooling bath was removed and 400 mL of saturated ammonium chloride solution was added to the reaction mixture.

후처리

  1. additionAfter complete addition
  2. stirringThis solution was stirred at -78° C. for one hour
  3. customThe cooling bath was removed
  4. addition400 mL of saturated ammonium chloride solution was added to the reaction mixture

출처 및 근거

ORD 기록
ord-52f922d09f9940b58a36c945d1a4e891
출처 데이터셋
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04761419

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