Water → 6-Bromo-7-chloro-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 1774834ノート

反応式

HRID 1774834 の反応式
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[NH:14][C:13](=[O:19])[CH2:12][CH2:11]2.CI.O>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]([CH3:1])[C:13](=[O:19])[CH2:12][CH2:11]2

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 709793626-Bromo-7-chloro-3,4-dihydroquinolin-2(1H)-one

生成物 1

HCID 866791856-Bromo-7-chloro-1-methyl-3,4-dihydro-1H-quinolin-2-one収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Potassium tert-butoxide (0.45 g, 4.0 mmol) was added to a solution of 6-bromo-7-chloro-3,4-dihydro-1H-quinolin-2-one (0.52 g, 2.0 mmol) in DMF (5 mL) at 0° C. Then, the reaction mixture was stirred at 0° C. for 30 min and methyl iodide (0.18 g, 1.29 mmol) was added. The resulting mixture was stirred for 2 hours before water was added. After extraction of the reaction mixture with EtOAc, the organic layer was washed with water and brine in sequence. Then, it was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to give a crude product (0.49 g, 90%) as a white solid. MS: 274.0 (M+H+)+.

後処理

  1. additionwas added
  2. extractionAfter extraction of the reaction mixture with EtOAc
  3. washthe organic layer was washed with water and brine in sequence
  4. dry with materialThen, it was dried over anhydrous Na2SO4
  5. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-3be3bf3437ab4d629f6cf74ce3801838
出典データセット
uspto-grants-2016_02
特許番号
US09260408B2

反応ノート

読み込み中…