Sodium ethoxide → 6-Bromo-4-ethoxyquinoline

HRID 852989ノート

反応式

HRID 852989 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[O-:13][CH2:14][CH3:15].[Na+]>C(O)C.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[O:13][CH2:14][CH3:15]

参加物

5

反応物 2

HCID 2723922Sodium ethoxideHCID 51395376-Bromo-4-chloroquinoline

生成物 1

HCID 586153986-Bromo-4-ethoxyquinoline収率 90.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
120 °C

実験手順

To a solution of 6-bromo-4-chloroquinoline (17 g, 70.10 mmol) in ethanol (400 mL) was added sodium ethoxide (23.85 g, 350.5 mmol) at room temperature. Then, the reaction mixture was heated to 120° C. for 15 h in a sealed reaction flask. After cooling to room temperature, the ethanol was removed under the vacuum and the residue was diluted with water. The aqueous suspension was neutralized with 3.0N hydrochloric acid until the precipitate formed and later it was diluted with saturated sodium bicarbonate solution. Then, the solids were collected by filtration and washed with water. After drying in air, 15.94 g (90.2% yield) of 6-bromo-4-ethoxy-quinoline was isolated as a white solid which can be crystallized from acetonitrile: EI-HRMS m/e calcd for C11H10BrNO (M+) 250.9946, found 250.9946.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe ethanol was removed under the vacuum
  3. additionthe residue was diluted with water
  4. customformed
  5. filtrationThen, the solids were collected by filtration
  6. washwashed with water
  7. customAfter drying in air

出典と根拠

ORDレコード
ord-5b83827849b44cdf8ee3784a67aae9a0
出典データセット
uspto-grants-2007_08
特許番号
US07253285B2

反応ノート

読み込み中…