3,4-dihydro-6-fluoro-9-(2-trifluoromethylbenzylamino)acridin-1(2H)-one → 1-Acridinol, 1,2,3,4-tetrahydro-6-fluoro-9-(((2-(trifluoromethyl)phenyl)methyl)amino)-

HRID 580740ノート

反応式

HRID 580740 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:27])([F:26])[F:25])=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][C:10]1=[O:28])=[N:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:25])([F:27])[F:26])=[C:11]1[C:6]([CH2:7][CH2:8][CH2:9][CH:10]1[OH:28])=[N:5]2

参加物

4

反応物 2

HCID 139351393,4-dihydro-6-fluoro-9-(2-trifluoromethylbenzylamino)acridin-1(2H)-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 30256251-Acridinol, 1,2,3,4-tetrahydro-6-fluoro-9-(((2-(trifluoromethyl)phenyl)methyl)amino)-収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a cooled solution of 5.7 g of 3,4-dihydro-6-fluoro-9-(2-trifluoromethylbenzylamino)acridin-1(2H)-one in 80 ml of tetrahydrofuran was added 7.5 ml of 1 molar solution of lithium aluminium hydride in THF. This was stirred for 0.5 hour and then quenched with 6 ml of saturated ammonium chloride solution. The inorganics were filtered, rinsed with ethyl acetate and the combined organics were dried over anhydrous magnesium sulfate. This was concentrated to a solid which was triturated with ether to give 5.1 g of a powder. This was twice recrystallized from ethyl acetate/hexane to give 3.1 g of analytically pure crystals, mp 149°-153° C.

後処理

  1. customquenched with 6 ml of saturated ammonium chloride solution
  2. filtrationThe inorganics were filtered
  3. washrinsed with ethyl acetate
  4. dry with materialthe combined organics were dried over anhydrous magnesium sulfate
  5. concentrationThis was concentrated to a solid which
  6. customwas triturated with ether

出典と根拠

ORDレコード
ord-1091a24cce5849dea32173be724ddd2c
出典データセット
uspto-grants-1988_06
特許番号
US04754050

反応ノート

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