Hydrochloric Acid → 6,7-Dimethoxy-2-isopropyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

HRID 1355646노트

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HRID 1355646 반응식
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1.[CH:17]([Mg]Cl)([CH3:19])[CH3:18].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>O1CCCC1>[CH2:26]([O:25][C:23]([N:6]1[C:7]2[C:12](=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=2)[C:3](=[O:2])[CH2:4][CH:5]1[CH:17]([CH3:19])[CH3:18])=[O:24])[CH3:27]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 154806724,6,7-TrimethoxyquinolineHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 696938456,7-Dimethoxy-2-isopropyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

4,6,7-Trimethoxyquinoline (0.3 g, 1.4 mmol) was dissolved in anhydrous tetrahydrofuran (6 mL). The mixture was cooled to −78° C., and isopropyl magnesium chloride (0.8 mL of a 2M solution in tetrahydrofuran, 1.6 mmol) was added. The mixture was stirred at −78° C. for 10 min, then ethyl chloroformate (0.16 mL, 1.6 mmol) was added. The reaction was warmed to room temperature and stirred overnight, then 1N HCl (6 mL) was added. After stirring for 1 h, the tetrahydrofuran was removed in vacuo, and the remaining aqueous phase was extracted with ethyl acetate (3×50 mL). The organic phases were combined and washed with water (15 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give 0.26 g crude product. Purification by silica gel chromatography using 0-40% ethyl acetate/hexanes as eluent afforded the title product (0.23 g, 51%). 1H NMR (CDCl3) δ 0.85 (d, 3H), 0.9 (d, 3H), 1.33 (t, 3H), 1.8 (m, 1H), 2.8 (dd, 1H), 2.93 (dd, 1H), 3.9 (s, 3H), 3.95 (s, 3H), 4.3 (m, 2H), 4.5 (m, 1H), 7.3 (bs, 1H), 7.37 (s, 1H).

후처리

  1. temperatureThe reaction was warmed to room temperature
  2. stirringstirred overnight
  3. stirringAfter stirring for 1 h
  4. customthe tetrahydrofuran was removed in vacuo
  5. extractionthe remaining aqueous phase was extracted with ethyl acetate (3×50 mL)
  6. washwashed with water (15 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give 0.26 g crude product
  11. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-0891ac97af704ac3bf920813ed7f0753
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586448B1

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