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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
ノート
印刷プレビュー

反応式

HRID 2309446 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 444266Maleic AcidHCID 13756055HCID 13756055、化合物HCID 21226445Aluminium lithium hydride

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283
Diethyl Ether
溶媒
HCID 3776Isopropanol溶媒2 回
HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b7e27fa45a08411d961896d2d861eabc
出典データセット
uspto-grants-1987_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04695573

反応ノート

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