HCID 13935138, 화합물 → 9-(((2-(Trifluoromethyl)phenyl)methyl)imino)-1,2,3,4,9,10-hexahydroacridin-1-ol

HRID 2309476노트

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HRID 2309476 반응식
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[C:19](=[O:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:20]=1[CH:19]([OH:21])[CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2

참가 물질

4

반응물 2

HCID 13935138HCID 13935138, 화합물HCID 21226445Aluminium lithium hydride

생성물 1

HCID 30256249-(((2-(Trifluoromethyl)phenyl)methyl)imino)-1,2,3,4,9,10-hexahydroacridin-1-ol수율 79.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
10 °C

실험 절차

In 100 ml of dry THF was dissolved 4.31 g of 3,4-dihydro-9-(2-trifluoromethylbenzylamino)acridin-1(2H)-one and the mechanically stirred solution was cooled to 10° C. under nitrogen. To it was added 5.8 ml of 1M LiAlH4 in THF dropwise over 15 minutes. Within 0.5 hour of addition the reaction was complete by TLC, so it was quenched with 1 ml of saturated ammonium chloride and the salts were filtered. The filtrate was evaporated to a solid which was dissolved in dichloromethane. The dichloromethane solution was dried over anhydrous magnesium sulfate and filtered. The filtrate was refluxed and pentane was added to effect crystallization. The crystals were collected from the cooled mother liquor to yield 3.44 g of solid, mp 158°-160° C.

후처리

  1. additionWithin 0.5 hour of addition the reaction
  2. customwas quenched with 1 ml of saturated ammonium chloride
  3. filtrationthe salts were filtered
  4. customThe filtrate was evaporated to a solid which
  5. dissolutionwas dissolved in dichloromethane
  6. dry with materialThe dichloromethane solution was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. temperatureThe filtrate was refluxed
  9. additionpentane was added to effect crystallization
  10. customThe crystals were collected from the cooled mother liquor

출처 및 근거

ORD 기록
ord-c9457bd1816641c7aec1539f90546e87
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04695573

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