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

HRID 1953455

반응식

HRID 1953455 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

HCID 2807468-Chloro-4-methylquinoline

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 702Ethanol용매

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온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2ad0e15a83d34a87a7d0ebbd602e5366
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06117884

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