Pyridine → 7-chloro-2,3-dihydro-l-(2-dimethylaminobenzoyl)-4(lH)-quinolinone

HRID 1073062

反応式

HRID 1073062 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.O1CCOCC1.[CH3:25][N:26]([CH3:36])[C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>ClCCl.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][N:9]2[C:29](=[O:30])[C:28]2[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=2[N:26]([CH3:25])[CH3:36])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 312751,4-DioxaneHCID 889747-Chloro-2,3-dihydro-4-quinoloneHCID 221579792-(Dimethylamino)benzoyl chloride

生成物 1

HCID 231668547-chloro-2,3-dihydro-l-(2-dimethylaminobenzoyl)-4(lH)-quinolinone収率 96.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 7-chloro-2,3-dihydro-4(lH)-quinolinone (20 g), pyridine (26 g) and dioxane (200 ml) was added dropwise 2-dimethylaminobenzoyl chloride (30 g) under cooling at 0° C. to 5° C. with stirring. The mixture was allowed to react at room temperature for additional 3 hours. The reaction mixture was poured into 500 ml of water, then shaken with additional dichloromethane (1000 ml). The organic layer was washed once with 1 N HCl (100 ml), twice with water (200 ml each) then once with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. Dichloromethane was removed in vacuo and the residue was recrystallized with dichloromethane and n-hexane to obtain 7-chloro-2,3-dihydro-l-(2-dimethylaminobenzoyl)-4(lH)-quinolinone (yield 35 g) as white crystal.

後処理

  1. temperatureunder cooling at 0° C. to 5° C.
  2. customto react at room temperature for additional 3 hours
  3. washThe organic layer was washed once with 1 N HCl (100 ml), twice with water (200 ml each)
  4. dry with materialonce with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate
  5. customDichloromethane was removed in vacuo
  6. customthe residue was recrystallized with dichloromethane and n-hexane

出典と根拠

ORDレコード
ord-2aee0c3fa5394b8281ce63ebaae96816
出典データセット
uspto-grants-1990_11
特許番号
US04968680

関連ノート

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