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

HRID 1763018
Notes
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Reaction equation

HRID 1763018 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent
HCID 3776IsopropanolSolvent2×
HCID 8028TetrahydrofuranSolvent

Procedure

In 75ml of dry tetrahydrofuran was dissolved 2.45 g of 9-phenethylamino-3,4-dihydroacridin-1(2H)-one. The solution was cooled in ice and 7.0ml (1 eq) of 1.1 M LiAlH4 in Et2O was added dropwise. After 0.5 hour the reaction was complete. It was neutralized with 0.5ml saturated NH4Cl solution and the resulting inorganic salts were filtered off. The filterate was evaporated to a solid and the maleate salt was found 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.

Workup

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

Sources & evidence

ORD record
ord-bd57e02bb2a540bdaa75dd4cc28ac036
Source dataset
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04835275

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes