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

HRID 1904737ノート

反応式

HRID 1904737 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]([F:33])([F:32])[C:9]1[CH:31]=[CH:30][CH:29]=[CH:28][C:10]=1[CH2:11][NH:12][C:13]1[C:14]2[C:19]([N:20]=[C:21]3[C:26]=1[C:25](=[O:27])[CH2:24][CH2:23][CH2:22]3)=[CH:18][CH:17]=[CH:16][CH:15]=2>C1COCC1>[F:32][C:8]([F:7])([F:33])[C:9]1[CH:31]=[CH:30][CH:29]=[CH:28][C:10]=1[CH2:11][NH:12][C:13]1[C:14]2[C:19]([N:20]=[C:21]3[C:26]=1[CH:25]([OH:27])[CH2:24][CH2:23][CH2:22]3)=[CH:18][CH:17]=[CH:16][CH:15]=2

参加物

4

反応物 2

HCID 13935138HCID 13935138、化合物HCID 21226445Aluminium lithium hydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ec1f6c1f44e9447abc92c3ab78ca4489
出典データセット
uspto-grants-1989_06
特許番号
US04839364

反応ノート

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