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Ammonium Chloride → 1-Acridinol, 1,2,3,4-tetrahydro-9-((2-phenylethyl)amino)-, (Z)-2-butenedioate (1:1) (salt)

HRID 2309446
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HRID 2309446 반응식
[CH2:1]([NH:9][C:10]1[C:11]2[C:16]([N:17]=[C:18]3[C:23]=1[C:22](=[O:24])[CH2:21][CH2:20][CH2:19]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37]>O1CCCC1.CCOCC.C(O)(C)C>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[CH2:1]([NH:9][C:10]1[C:11]2[C:16]([N:17]=[C:18]3[C:23]=1[CH:22]([OH:24])[CH2:21][CH2:20][CH2:19]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 444266Maleic AcidHCID 13756055HCID 13756055, 화합물HCID 21226445Aluminium lithium hydride

생성물 1

HCID 137560631-Acridinol, 1,2,3,4-tetrahydro-9-((2-phenylethyl)amino)-, (Z)-2-butenedioate (1:1) (salt)수율 32%

시약·촉매·용매 3

HCID 3283
Diethyl Ether
용매
HCID 3776Isopropanol용매2회
HCID 8028Tetrahydrofuran용매

실험 절차

In 75 ml of dry tetrahydrofuran was dissolved 2.45 g of 9-phenethylamino-3,4-dihydroacridin-1-(2H)-one. The solution was cooled in ice and 7.0 ml (1 eq) of 1.1M LiAlH4 in Et2O was added dropwise. After 0.5 hour the reaction was complete. It was neutralized with 0.5 ml saturated NH4Cl solution and the resulting inorganic salts were filtered off. The filtrate was evaporated to a solid and the meleate salt was formed by adding a solution of 1.1 eq maleic acid in isopropanol to a suspension of the product in isopropanol. A solution formed initially but the salt precipitated out over 0.5 hour at ambient temperatures. The salt was filtered off and recrystallized from 5:1 EtOAc/MeOH and dried at 80° C. in vacuo to yield 1.14 g (32%) of a solid, melting point 169° C.

후처리

  1. temperatureThe solution was cooled in ice
  2. filtrationthe resulting inorganic salts were filtered off
  3. customThe filtrate was evaporated to a solid
  4. customthe meleate salt was formed
  5. customA solution formed initially
  6. customthe salt precipitated out over 0.5 hour at ambient temperatures
  7. filtrationThe salt was filtered off
  8. customrecrystallized from 5:1 EtOAc/MeOH
  9. customdried at 80° C. in vacuo

출처 및 근거

ORD 기록
ord-b7e27fa45a08411d961896d2d861eabc
출처 데이터셋
uspto-grants-1987_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04695573

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