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

HRID 1763041노트

반응식

HRID 1763041 반응식
[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

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 13935131HCID 13935131, 화합물HCID 16211445Aluminum;lithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1c778142f18943028aba466618f328bd
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04835275

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