Ethanol → 2-chloro-1H-indole-3-carbonitrile

HRID 128831

반응식

HRID 128831 반응식
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.Cl.NO.[N:16]1C=CC=CC=1.CCO>CC(OC(C)=O)=O.O>[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]#[N:16])=[CH:8][CH:7]=[CH:6][CH:5]=2

참가 물질

7

반응물 4

HCID 702EthanolHCID 1049PyridineHCID 3147912-chloro-1H-indole-3-carbaldehydeHCID 443297Hydroxyamine hydrochloride

생성물 1

HCID 103298542-chloro-1H-indole-3-carbonitrile수율 58%

시약·촉매·용매 2

HCID 962Water용매HCID 7918Acetic Anhydride용매

실험 절차

A mixture of 2-chloroindole-3-carboxaldehyde (7.0 g, 36 mmol) was reacted with a slight excess of hydroxylamine hydrochloride and pyridine in refluxing EtOH for 1 hour, to give the crude oxime (Latrell R, Bartmann W, Musif J, Granzer E, German Patent 2,707,268, 31 Aug 1978, Chem. Abstr. 1978;89:179858y). A solution of this in Ac2O (100 mL) was heated under reflux for 1 hour, cooled, and stirred with water (700 mL). The precipitated solid was collected, washed with water, and crystallized from aqueous MeOH to give 2-chloro-1H-indole-3-carbonitrile (3.7 g, 58%); mp 177°-180° C.

후처리

  1. customto give the crude oxime (Latrell R, Bartmann W, Musif J, Granzer E, German Patent 2,707,268, 31 Aug 1978, Chem. Abstr. 1978;89:179858y)
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. customThe precipitated solid was collected
  5. washwashed with water
  6. customcrystallized from aqueous MeOH

출처 및 근거

ORD 기록
ord-3e3748a6eb08424ebcc6169c3886b319
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464861

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