Sodium ethoxide → 6-Bromo-4-ethoxyquinoline

HRID 852989노트

반응식

HRID 852989 반응식
[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]

참가 물질

5

반응물 2

HCID 2723922Sodium ethoxideHCID 51395376-Bromo-4-chloroquinoline

생성물 1

HCID 586153986-Bromo-4-ethoxyquinoline수율 90.2%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 516892Sodium Bicarbonate용매

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5b83827849b44cdf8ee3784a67aae9a0
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253285B2

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