Ammonium Chloride → 9-(((3-(Trifluoromethyl)phenyl)methyl)imino)-1,2,3,4,9,10-hexahydroacridin-1-ol

HRID 2309478노트

반응식

HRID 2309478 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl-].[NH4+].[F:9][C:10]([F:35])([F:34])[C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][CH:33]=1)[CH2:14][NH:15][C:16]1[C:17]2[C:22]([N:23]=[C:24]3[C:29]=1[C:28](=[O:30])[CH2:27][CH2:26][CH2:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2>C1COCC1>[F:34][C:10]([F:9])([F:35])[C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][CH:33]=1)[CH2:14][NH:15][C:16]1[C:17]2[C:22]([N:23]=[C:24]3[C:29]=1[CH:28]([OH:30])[CH2:27][CH2:26][CH2:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 13935142HCID 13935142, 화합물HCID 21226445Aluminium lithium hydride

생성물 1

HCID 30256269-(((3-(Trifluoromethyl)phenyl)methyl)imino)-1,2,3,4,9,10-hexahydroacridin-1-ol수율 80.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

In 100 ml dry THF was dissolved in 3.86 g of 3,4-dihydro-9-(3-trifluoromethylbenzyl)aminoacridin-1(2H)-one. The solution was stirred mechanically under nitrogen and cooled in ice. To it was added 5.2 ml of 1M LiAlH4 in THF dropwise. After stirring an additional 0.5 hour, the reaction was complete. It was neutralized with 1 ml of saturated ammonium chloride and the salts were filtered off. The THF filtrate was evaporated to an oil which solidified upon trituration with pentane. The solid was recrystallized from 1:1 dichloromethane/pentane to yield 3.12 g of solid, mp 154°-155° C.

후처리

  1. temperaturecooled in ice
  2. stirringAfter stirring an additional 0.5 hour
  3. filtrationthe salts were filtered off
  4. customThe THF filtrate was evaporated to an oil which
  5. customThe solid was recrystallized from 1:1 dichloromethane/pentane

출처 및 근거

ORD 기록
ord-bc5eeb6e24244288bf4021761945cf89
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04695573

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