3-Bromoquinoline → 3-(Dimethoxyacetyl)quinoline

HRID 34745

反応式

HRID 34745 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 142769343-(Dimethoxyacetyl)quinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-97c01dee82af4b81ba08bf372d90172a
出典データセット
uspto-grants-1988_08
特許番号
US04762921

関連ノート

読み込み中…