Sodium Carbonate → HCID 10636627, compound

HRID 1241695Notes

Reaction equation

HRID 1241695 reaction equation
CC(C)(C)C(NC1C=CC=CC=1[C:12]1[C:25]2[C:24](=O)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH3:27])[C:16]=2[CH:15]=[CH:14][CH:13]=1)=O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH3:27][N:17]1[C:16]2[C:25]3[C:12](=[C:15]4[C:16](=[N:17][C:24]=3[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]1=3)[CH:25]=[CH:12][CH:13]=[CH:14]4)[CH:13]=[CH:14][CH:15]=2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 10927115HCID 10927115, compound2×

Product 1

HCID 10636627HCID 10636627, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Method H-2) (Cyclisation) 2,2-Dimethyl-N-[2-(10-methyl-9-oxo-9,10-dihydro-acridin-1-yl)-phenyl]-propionamide, 25 (50 mg, 0.13 mmol) was dissolved in 1:1 THF/6N HCl (20 mL) and the mixture heated to reflux for 5 days giving a bright orange solution. The mixture was basified (aq. Na2CO3) and extracted with ethyl acetate (50 mL) and the organic layer dried (Na2SO4), and evaporated under reduced pressure. The crude product was purified by column chromatography (1:4 EtOAc: hexane) to give the title compound as a yellow solid (35 mg, 0.12 mmol, 95%).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 5 days
  3. customgiving a bright orange solution
  4. extractionextracted with ethyl acetate (50 mL)
  5. dry with materialthe organic layer dried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography (1:4 EtOAc: hexane)

Sources & evidence

ORD record
ord-92a1c5a23df047dd8f818f00490c16ed
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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