Dimethyl acetylenedicarboxylate → 2-(Methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinoline

HRID 348067

반응식

HRID 348067 반응식
[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH3:10].[C:11]([C:17](OC)=[O:18])#[C:12][C:13]([O:15][CH3:16])=[O:14]>CO>[CH3:16][O:15][C:13]([C:12]1[CH2:11][C:17](=[O:18])[C:6]2[C:7](=[C:2]([Cl:1])[C:3]([CH3:10])=[C:4]([Cl:9])[CH:5]=2)[N:8]=1)=[O:14]

참가 물질

4

반응물 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 882822,4-Dichloro-m-toluidine

생성물 1

HCID 684344222-(Methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinoline수율 90.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 2,6-dichloro-3-aminotoluene (20.5 g, 0.11 mol) in methanol (300 mL) was added dimethyl acetylenedicarboxylate (15 mL, 0.12 mol) and the reaction mixture was refluxed for 2 hours. The reaction mixture was concentrated under reduced pressure to a yellow solid. Diphenyl ether (350 mL) was heated to 230–240° C., and the yellow solid was added to it. The temperature was maintained at 230–240° C. for 20 minutes and the reaction mixture was cooled slowly to ambient temperature and diluted with petroleum ether (1L). The solid was filtered and washed with hot ethyl acetate to afford a brown solid, 2-(methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinoline (28.5 g, 85%); NMR (CDCl3) 2.62 (s, 3), 4.04 (s, 3), 7.02 (s, 1), 8.24 (s, 1) ppm.

후처리

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure to a yellow solid
  3. temperatureDiphenyl ether (350 mL) was heated to 230–240° C.
  4. additionthe yellow solid was added to it
  5. temperatureThe temperature was maintained at 230–240° C. for 20 minutes
  6. additiondiluted with petroleum ether (1L)
  7. filtrationThe solid was filtered
  8. washwashed with hot ethyl acetate

출처 및 근거

ORD 기록
ord-06cacf47c12544189dd6e804d4d25e23
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176207B2

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