Sodium Hydroxide → 4-Chloroquinoline-6-carbonitrile

HRID 1072874ノート

反応式

HRID 1072874 の反応式
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[N:10]=[CH:9][CH:8]=1.[OH-].[Na+]>CN(C=O)C>[Cl:3][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[N:10]=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 116583514-Hydroxyquinoline-6-carbonitrile

生成物 1

HCID 204935814-Chloroquinoline-6-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Phosphorus oxychloride (0.518 ml) was added to DMF (9 ml) at an inner temperature of 5-7° C. while stirring under ice-cooling, and the mixture was stirred at room temperature for 0.5 hr. 4-Hydroxy-6-quinolinecarbonitrile (860 mg) was added while stirring under ice-cooling and the mixture was stirred under ice-cooling for 1 hr. 1N aqueous sodium hydroxide solution (18 ml) was added and the mixture was stirred at room temperature for 10 min. The precipitate was collected by filtration and washed with water to give a pale brown powder. The obtained powder was purified by silica gel column chromatography (eluent: chloroform-methanol=50/1) to give the object compound (800 mg) as a pale yellow powder.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 0.5 hr
  3. stirringwhile stirring under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred under ice-
  6. temperaturecooling for 1 hr
  7. stirringthe mixture was stirred at room temperature for 10 min
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with water
  10. customto give a pale brown powder
  11. customThe obtained powder was purified by silica gel column chromatography (eluent: chloroform-methanol=50/1)

出典と根拠

ORDレコード
ord-1efc1bbb7f86419e81b76ba741b0d6a0
出典データセット
uspto-grants-2005_06
特許番号
US06911469B2

反応ノート

読み込み中…