Chloroform → Ethyl 4,5,7-trichloro-8-methoxyquinoline-3-carboxylate

HRID 1436964노트

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HRID 1436964 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][CH:12]=C[C:10]=2[O:17][CH3:18])=[O:5])[CH3:2].S(Cl)([Cl:22])(=O)=O.[CH:24]([Cl:27])(Cl)Cl>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[C:13]([Cl:22])[CH:12]=[C:24]([Cl:27])[C:10]=2[O:17][CH3:18])=[O:5])[CH3:2]

참가 물질

4

반응물 3

HCID 6212Chloroform2회HCID 24648Sulfuryl chloride2회HCID 3045573-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl ester

생성물 1

HCID 57939336Ethyl 4,5,7-trichloro-8-methoxyquinoline-3-carboxylate수율 29%

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온도
65 °C

실험 절차

To a stirred solution of 4-chloro-8-methoxy-quinoline-3-carboxylic acid ethyl ester (1.00 g, 3.76 mmol) in chloroform (50 mL) was added, dropwise over 1 h, a solution of sulfuryl chloride (15 mL) in chloroform (15 mL) whilst maintaining the temperature at 25-30° C. The solution was then heated at 60-70° C. for 48 h. During this time, further sulfuryl chloride (2 mL) was added at regular intervals (2, 24 and 30 h). The solution was allowed to cool to RT and added to ice-aqueous ammonia, adjusting the pH to 8. The mixture was then extracted with dichloromethane (20 mL×3), the extracts combined and concentrated. Column chromatography (silica gel, dichloromethane/methanol (100:1)) gave the title compound 26 as a cream solid (0.36 g, 29%). 1H-NMR (CDCl3, 400 MHz): δ 9.04 (s, 1H), 7.78 (s, 1H), 4.51 (q, J=7.1, 2 H), 4.14 (s, 3H), 1.46 (t, J=7.1, 3 H).

후처리

  1. temperatureto cool to RT
  2. additionadded to ice-aqueous ammonia
  3. extractionThe mixture was then extracted with dichloromethane (20 mL×3)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-00581099ada44d629d3952f5c9300f0c
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07619091B2

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