3-Bromoquinoline → 3-(Dimethoxyacetyl)quinoline

HRID 34745

반응식

HRID 34745 반응식
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([Li])CCC.[CH3:17][O:18][CH:19]([O:28][CH3:29])[C:20](N1CCOCC1)=[O:21]>C1COCC1>[CH3:17][O:18][CH:19]([O:28][CH3:29])[C:20]([C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:21]

참가 물질

5

반응물 3

HCID 214133-BromoquinolineHCID 21298597N-(dimethoxyacetyl)morpholineHCID 178418339Butyllithium

생성물 1

HCID 142769343-(Dimethoxyacetyl)quinoline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3-Bromoquinoline (3.29 ml., 0.032 mol) was dissolved in 300 ml. THF and cooled to -78°. n-Butyllithium (13.6 ml. of 2.5M in hexane, 0.034 ml.) was added slowly and the mixture stirred 15 minutes at -75° to -78°. N-(Dimethoxyacetyl)morpholine (5.98 g., 0.032 mol) in 10 ml. THF was then added and stirring continued for 1.75 hours at the same temperature. The reaction was then quenched into 300 ml. saturated NH4Cl. The aqueous layer was separated and extracted 4×100 ml. ether. The organic layers were combined, dried over MgSO4, stripped to yield title product, 7.0 g., bp 120°-123°/0.125 torr.

후처리

  1. stirringstirring
  2. waitcontinued for 1.75 hours at the same temperature
  3. customThe reaction was then quenched into 300 ml
  4. customThe aqueous layer was separated
  5. extractionextracted 4×100 ml
  6. dry with materialdried over MgSO4

출처 및 근거

ORD 기록
ord-97c01dee82af4b81ba08bf372d90172a
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04762921

연결된 노트

불러오는 중…