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

HRID 915184

反応式

HRID 915184 の反応式
[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].[CH2:18](I)C.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]

参加物

6

反応物 4

HCID 962WaterHCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 219664237-Bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one

生成物 1

HCID 219664297-bromo-1,4,4,6-tetramethyl-3,4-dihydro-1H-quinoline-2-one収率 104.5%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
0 °C

実験手順

A mixture of powdered potassium hydroxide (3.35 g, 59.67 mmol) in DMSO (40 mL) was stirred at 0° C. for 10 min. 7-bromo-4,4,6-trimethyl-3,4-dihydro-1H-quinoline-2-one (Example 2c) (8.0 g, 29.83 mmol) was added cautiously, followed immediately by the addition of ethyl iodide (12 mL, 149.17 mmol). 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 (Mg2SO4), filtered and evaporated to give 8.8 g of 7-bromo-1,4,4,6-tetramethyl-3,4-dihydro-1H-quinoline-2-one and used without further purification in the Suzuki coupling (step a). 1H NMR (300 MHz; CDCl3): 1.24 (t, J=7.2 Hz, 1 H), 1.25 (s, 6 H), 2.37 (s, 3 H), 2.45 (s, 2 H), 3.98 (q, 2 H), 7.13 (s, 1 H), 7.18 (s, 1 H).

後処理

  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 (Mg2SO4)
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-2409a829d379468393ded1b92a9a238c
出典データセット
uspto-grants-2007_09
特許番号
US07265139B2

関連ノート

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