Ammonium Chloride → 1-Acridinol, 1,2,3,4-tetrahydro-9-(((3-fluorophenyl)methyl)amino)-

HRID 1763041ノート

反応式

HRID 1763041 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=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.[Al].[Li].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=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

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 13935131HCID 13935131、化合物HCID 16211445Aluminum;lithium

生成物 1

HCID 30256191-Acridinol, 1,2,3,4-tetrahydro-9-(((3-fluorophenyl)methyl)amino)-収率 0.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In 100 ml of THF was dissolved 300 g of 3,4-dihydro-9-(3-fluorobenzylamino)acridin-1(2H)-one. The mechanically stirred solution was cooled in ice under nitrogen and 4.68 ml of 1M lithium aluminum hidride in THF was added dropwise over 15 minutes. After 0.5 hours, analysis by TLC indicated the reaction was complete, so it was neutralized with 1 ml of saturated ammonium chloride solution and the resulting salts were filtered. The filtrate was evaported to an oil which crystallized on trituration with pentane. The solid was filtered and recrystallized from 1:1 dichloromethane/pentane to yield 2.50 g of solid, mp 128° C.

後処理

  1. temperatureThe mechanically stirred solution was cooled in ice under nitrogen
  2. filtrationthe resulting salts were filtered
  3. customcrystallized on trituration with pentane
  4. filtrationThe solid was filtered
  5. customrecrystallized from 1:1 dichloromethane/pentane

出典と根拠

ORDレコード
ord-1c778142f18943028aba466618f328bd
出典データセット
uspto-grants-1989_05
特許番号
US04835275

反応ノート

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