Ammonium Hydroxide → 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline

HRID 255568

反応式

HRID 255568 の反応式
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:15]([O-])=[CH:14][C:13]=2[N:12]=[CH:11]1)[CH:7]([CH3:9])[CH3:8].[OH-].[NH4+]>CN(C)C=O>[Cl:3][C:14]1[C:13]2[N:12]=[CH:11][N:10]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 118315721-isobutyl-1H-imidazo[4,5-c]quinoline-5-oxide

生成物 1

HCID 3839614-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline収率 89.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 40 ml of cold N,N-dimethylformamide (10°-20° C.) was added slowly 5.9 g (0.0385 mole) of phosphorus oxychloride with swirling, the temperature of the mixture being maintained at 10°-20° C. 1-Isobutyl-1H-imidazo[4,5-c]quinolin-5-oxide (6.2 g; 0.0257 mole) from Step (C) above was added gradually with swirling and cooling. After addition was complete, the solution was allowed to stand at room temperature for about 30 minutes with occasional swirling. The solution was then heated on a steam bath for thirty minutes. After allowing it to cool, the solution was poured onto ice with stirring, and the resulting mixture was brought to pH 8-9 with concentrated ammonium hydroxide. The resulting off-white solid was filtered, washed with water, rinsed with ether, and dried to provide 6.0 g of crude 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline having a m.p. of 135°-138° C.

後処理

  1. temperaturethe temperature of the mixture being maintained at 10°-20° C
  2. temperaturecooling
  3. additionAfter addition
  4. temperatureThe solution was then heated on a steam bath for thirty minutes
  5. temperatureto cool
  6. additionthe solution was poured onto ice
  7. filtrationThe resulting off-white solid was filtered
  8. washwashed with water
  9. washrinsed with ether
  10. customdried

出典と根拠

ORDレコード
ord-524934cd5e0d4d0ba9c400a2fc2c3436
出典データセット
uspto-grants-1987_10
特許番号
US04698348

関連ノート

読み込み中…