Dimethylformamide → 9-Amino-7-chloro-3,4-dihydroacridin-1(2H)-one

HRID 1249414

Reaction equation

HRID 1249414 reaction equation
CN(C)C=O.Cl.[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([NH:16][C:17]2[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH:18]=2)=[C:12]([CH:15]=1)[C:13]#[N:14].O=C1CCCC(NC2C=CC=CC=2C#N)=C1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[NH2:14][C:13]1[C:12]2[C:11]([N:16]=[C:17]3[C:18]=1[C:19](=[O:23])[CH2:20][CH2:21][CH2:22]3)=[CH:10][CH:9]=[C:8]([Cl:7])[CH:15]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 184360Benzonitrile, 2-((3-oxo-1-cyclohexen-1-yl)amino)-HCID 200377145-Chloro-2-(3-oxocyclohexen-1-yl)aminobenzonitrile hydrochloride

Product 1

HCID 137560579-Amino-7-chloro-3,4-dihydroacridin-1(2H)-oneYield 4.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 5 liters of toluene were combined 200 ml of dimethylformamide, 180.71 g of 5-chloro-2-(3-oxocyclohexen-1-yl)aminobenzonitrile hydrochloride prepared in the same manner as the compounds of EXAMPLES 1 and 2, 176 g (2 eq) of milled K2CO3 and 3 g of cuprous chloride (CuCl). After 6 hours of reflux a little reaction occurred, so 3 g more of CuCl was added. After 12 hours of reflux more product had slowly formed. In order to hasten the reaction, 3 g more of CuCl was added. After overnight reflux the reaction mixture was evaporated and the residue extracted with dichloromethane via a Soxhlet extraction apparatus for 12 hours. The dichloromethane solution was evaporated to a solid. The solid was suspended in water and H2SO4 was added. The resultant salt which precipitated out, was filtered and made basic with 10% NaOH. The solid was filtered and recrystallized twice from isopropanol/toluene to yield 6.84 g (4%) of a solid, melting point over 260° C.

Workup

  1. temperatureAfter 6 hours of reflux
  2. customa little reaction
  3. temperatureAfter 12 hours of reflux more product
  4. customhad slowly formed
  5. additionwas added
  6. temperatureAfter overnight reflux the reaction mixture
  7. customwas evaporated
  8. extractionthe residue extracted with dichloromethane via a Soxhlet extraction apparatus for 12 hours
  9. customThe dichloromethane solution was evaporated to a solid
  10. additionH2SO4 was added
  11. customThe resultant salt which precipitated out
  12. filtrationwas filtered
  13. filtrationThe solid was filtered
  14. customrecrystallized twice from isopropanol/toluene

Sources & evidence

ORD record
ord-e627d7dbe1c944648a32e0d17363d775
Source dataset
uspto-grants-1986_12
Patent number
US04631286

Linked notes

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