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

HRID 1763016Notes

Reaction equation

HRID 1763016 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([NH:15][C:16]2[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH:17]=2)=[C:11]([CH:14]=1)[C:12]#[N:13].O=C1CCCC(NC2C=CC=CC=2C#N)=C1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[NH2:13][C:12]1[C:11]2[C:10]([N:15]=[C:16]3[C:17]=1[C:18](=[O:22])[CH2:19][CH2:20][CH2:21]3)=[CH:9][CH:8]=[C:7]([Cl:6])[CH:14]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 184360Benzonitrile, 2-((3-oxo-1-cyclohexen-1-yl)amino)-HCID 145001865-Chloro-2-(3-oxocyclohexen-1-yl)amino-benzonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 5 liters of toluene were combined 200ml of dimethyl-formamide, 180.71 g of 5-chloro-2-(3-oxocyclohexen-1-yl)amino-benzonitrile hydrochloroide 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 3 g more of CuCl was added. After 12 hours of reflux 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 overnight reflux the reaction mixture
  2. customwas evaporated
  3. extractionthe residue extracted with dichloromethane via a Soxhlet extraction apparatus for 12 hours
  4. customThe dichloromethane solution was evaporated to a solid
  5. additionH2SO4 was added
  6. customThe resultant salt which precipitated out
  7. filtrationwas filtered
  8. filtrationThe solid was filtered
  9. customrecrystallized twice from isopropanol/toluene

Sources & evidence

ORD record
ord-a20a6eee3836462db3fe44818a0839af
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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