Water → 7-bromo-1,4,4,6-tetramethyl-3,4-dihydro-1H-quinoline-2-one

HRID 2212579

반응식

HRID 2212579 반응식
[OH-].[K+].[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([CH3:16])([CH3:15])[CH2:9][C:10](=[O:14])[NH:11]2)=[CH:6][C:5]=1[CH3:17].[CH3:18]I.O>CS(C)=O>[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([CH3:15])([CH3:16])[CH2:9][C:10](=[O:14])[N:11]2[CH3:18])=[CH:6][C:5]=1[CH3:17]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 219664237-Bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one

생성물 1

HCID 219664297-bromo-1,4,4,6-tetramethyl-3,4-dihydro-1H-quinoline-2-one수율 101.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
0 °C

실험 절차

A mixture of powdered KOH (14.06 g, 0.250 mol) in DMSO (150 mL) was stirred at 0° C. for 10 min. 7-Bromo-4,4,6-trimethyl-3,4- dihydro-1H-quinoline-2-one (33.59 g, 0.125 mol) was added cautiously, followed immediately by the addition of methyl iodide (39 mL, 0.625 mol). The reaction mixture was kept at 0° C. for 30 min then slowly warmed up to room temperature and stirred overnight at room temperature. The reaction mixture was poured into water and extracted with dichloromethane washed with water and brine, dried (MgSO4), filtered and evaporated to give 35.74 g of 7-bromo-1,4,4,6-tetramethyl-3,4-dihydro-1H-quinoline-2-one (99%) and used without further purification in the Suzuki coupling (step a). 1H NMR (300 MHz; CDCl3): 1.27 (s, 6 H), 2.37 (s, 3 H), 2.48 (s, 2 H), 3.35 (s, 3 H), 7.12 (s, 1 H), 7.16 (s, 1 H).

후처리

  1. waitThe reaction mixture was kept at 0° C. for 30 min
  2. temperaturethen slowly warmed up to room temperature
  3. stirringstirred overnight at room temperature
  4. extractionextracted with dichloromethane
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-831371cfd739469e9a970254baefab82
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07102000B2

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