Potassium Carbonate → 9-amino-3,4-dihydroacridin-1(2H)-one

HRID 1763002Notes

Reaction equation

HRID 1763002 reaction equation
Cl.[O:2]=[C:3]1[CH2:8][CH2:7][CH2:6][C:5]([NH:9][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])=[CH:4]1.C([O-])([O-])=O.[K+].[K+]>O1CCCC1.Cl[Cu]>[NH2:13][C:12]1[C:11]2[C:10]([N:9]=[C:5]3[C:4]=1[C:3](=[O:2])[CH2:8][CH2:7][CH2:6]3)=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 13756047HCID 13756047, compound

Product 1

HCID 1843619-amino-3,4-dihydroacridin-1(2H)-oneYield 41.4%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In 2 liters of tetrahydrofuran were combined 219.3 g of 2-(3-oxocyclohexen-1-yl)aminobenzonitrile hydrochloride, 250 g (2 eq) of milled K2CO3, and 3 g of CuCl catalyst. The mechanically stirred mixture was refluxed 5 hours and then filtered hot to remove the inorganic salts. The filtrate was evaporated to a residue and the residue was recrystallized twice from isopropanol to yield 77.4 g (41%) of a powder, melting point 236°-238° C.

Workup

  1. temperatureThe mechanically stirred mixture was refluxed 5 hours
  2. filtrationfiltered hot
  3. customto remove the inorganic salts
  4. customThe filtrate was evaporated to a residue
  5. customthe residue was recrystallized twice from isopropanol

Sources & evidence

ORD record
ord-d5c68d77a4fc4749ad635782cfaba02c
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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