2-Chloroaniline hydrochloride → 8-Chloro-4-methylquinoline

HRID 1953455

反応式

HRID 1953455 の反応式
Cl.[Cl:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].CO[CH2:12][CH2:13][C:14](OC)(OC)[CH3:15]>[Cl-].[Zn+2].[Cl-].C(O)C>[Cl:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:4]=1[N:5]=[CH:12][CH:13]=[C:14]2[CH3:15]

参加物

5

反応物 2

HCID 672982-Chloroaniline hydrochlorideHCID 810844-Methoxybutan-2-one-dimethylacetal

生成物 1

HCID 2807468-Chloro-4-methylquinoline

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

Commercially available 2-chloroaniline (200 g, 1.56 mol) was dissolved in 600 ml ethanol, and dry HCl gas was bubbled through for 10 minutes to give 2-chloroaniline hydrochloride. A new flask was charged with 2-chloroaniline hydrochloride (130 g, 0.793 mol), ferric chloride hexahydrate (25.7 g, 0.095 mol), anhydrous zinc chloride (10.9 g, 0.0799 mol) and 500 ml 2B ethanol. The mixture was heated to 60° C. for 10 minutes and 1,3,3-trimethoxy butane was added dropwise over a period of one hour. The mixture was then refluxed for two hours and allowed to stand overnight at room temperature. Most of the alcohol was removed by distillation and the residue was made alkaline with 25% sodium hydroxide solution. The reaction was cooled, filtered, and the filter pad washed with toluene. The toluene was concentrated to dryness. The product was recrystallized from dichloromethane/pentane to obtained a spectroscopically pure sample (mp: 110° C., 37.0 g, 25% overall yield).

後処理

  1. temperatureThe mixture was then refluxed for two hours
  2. customMost of the alcohol was removed by distillation
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. washthe filter pad washed with toluene
  6. concentrationThe toluene was concentrated to dryness
  7. customThe product was recrystallized from dichloromethane/pentane
  8. customto obtained
  9. customa spectroscopically pure sample (mp: 110° C., 37.0 g, 25% overall yield)

出典と根拠

ORDレコード
ord-2ad0e15a83d34a87a7d0ebbd602e5366
出典データセット
uspto-grants-2000_09
特許番号
US06117884

関連ノート

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