Ammonium Chloride → Suronacrine

HRID 580701노트

반응식

HRID 580701 반응식
[CH2:1]([NH:8][C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[C:21](=[O:23])[CH2:20][CH2:19][CH2:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].[NH4+].[Cl-]>O1CCCC1.CCOCC>[CH2:1]([NH:8][C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[CH:21]([OH:23])[CH2:20][CH2:19][CH2:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 166653HydrideHCID 41342583,4-DIHYDRO-9-[(BENZYL)AMINO]-1(2H)-ACRIDINONEHCID 21226445Aluminium lithium hydride

생성물 1

HCID 60601Suronacrine수율 75.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

In 75 ml of dry tetrahydrofuran was dissolved 3.81 g of 9-benzylamino-3,4-dihydroacridin-1(2H)-one with mechanical stirring. The solution was cooled in ice under N2 and 5.9 ml (0.5 eq) of 1.1M LiAlH4 solution in ether was added dropwise. After 0.5 hour the reaction was complete based on thin layer chromatography analysis. The excess hydride was neutralized with 0.5 ml of saturated NH4Cl solution and the inorganic salts were extracted into 30% potassium hydroxide. The tetrahydrofuran solution was decanted and evaporated to a solid which was recrystallized from 1:10 dichloromethane/EtOAc to yield 2.89 g (75%) of a solid, melting point 159° C.

후처리

  1. temperatureThe solution was cooled in ice under N2
  2. extractionthe inorganic salts were extracted into 30% potassium hydroxide
  3. customThe tetrahydrofuran solution was decanted
  4. customevaporated to a solid which
  5. customwas recrystallized from 1:10 dichloromethane/EtOAc

출처 및 근거

ORD 기록
ord-54ed7c0c759f4a38aca4ca74123e9962
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04754050

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