Ammonium Chloride → Suronacrine

HRID 580701ノート

反応式

HRID 580701 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 60601Suronacrine収率 75.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-54ed7c0c759f4a38aca4ca74123e9962
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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