4-Chloroaniline → HCID 57289360、化合物

HRID 28670

反応式

HRID 28670 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N:9]([O-])=O.[Na+].OC=[C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16]1=[O:21].C([O-])(=O)C.[Na+]>Cl.O.CO>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][N:9]=[C:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]2=[O:21])=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 78124-ChloroanilineHCID 101871Cyclohexanone, 2-(hydroxymethylene)-HCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

生成物 1

HCID 57289360HCID 57289360、化合物収率 49%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

To a cold (0° C.) solution of 4-chloroaniline (5.6 g, 44 mmol) in concentrated hydrochloric acid (5 mL) was added sodium nitrite (3.0 g, 44 mmol) dissolved in water (10 mL) portionwise over 20 minutes. The mixture was stirred at 0° C. for 30 minutes. In a separate flask, a cool solution of 2-(hydroxymethylene)cyclohexanone (Organic Syntheses, Collective Vol 4, 1963, pg. 536) (5.0 g, 40 mmol) in methanol (30 mL) was treated with a solution of sodium acetate (8.3 g, 101 mmol) in water (25 mL). The mixture was stirred at 0° C. for 20 minutes and the diazonium salt slurry was added. The combined mixture was stirred for 10-15 minutes, collected by filtration, triturated with ethanol, and collected by filtration to give cyclohexane-1,2-dione (4-chlorophenyl)hydrazone (4.6 g, 49% yield) as a yellow solid. 1H-NMR (DMSO-d6): δ 9.93 (s, 1H), 7.29 (m, 4H), 2.55 (m, 2H), 2.40 (m, 2H), 1.84-1.75 (m, 4H).

後処理

  1. stirringThe mixture was stirred at 0° C. for 20 minutes
  2. stirringThe combined mixture was stirred for 10-15 minutes
  3. filtrationcollected by filtration
  4. customtriturated with ethanol
  5. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-1d2fae41e866434da2bf685100ac5eb4
出典データセット
uspto-grants-2008_09
特許番号
US07419997B2

関連ノート

読み込み中…