Sodium Hydroxide → 6-Ethyl-2,3-dihydroquinolin-4(1H)-one

HRID 1985089Notes

Reaction equation

HRID 1985089 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH2:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH2:24][CH2:25][C:26]([O:28]CC)=O)=[CH:19][CH:18]=1)[CH3:16].[OH-].[Na+]>CS(O)(=O)=O.CO>[CH2:15]([C:17]1[CH:18]=[C:19]2[C:20](=[CH:21][CH:22]=1)[NH:23][CH2:24][CH2:25][C:26]2=[O:28])[CH3:16]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)2×HCID 43365416HCID 43365416, compound

Product 1

HCID 223244436-Ethyl-2,3-dihydroquinolin-4(1H)-oneYield 28%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of phosphorus pentoxide (11.14 g) in methane sulfonic acid (114 mL) was heated to 1300. The mixture was stirred at 130° for one hour until all the phosphorus pentoxide had dissolved. The mixture was allowed to cool for 15 minutes, and ethyl N-(4-ethylphenyl)-beta-alaninate (11.14 g of mono and di-ester mixture) was added. The mixture was heated to 130° for 1.5 hours, and the mixture was allowed to cool to room temperature. The mixture was cooled in an ice bath, and 50% sodium hydroxide was added until the pH reached 8. The gummy dark solids were dissolved in MeOH, and added to the mixture. Solids began to crash out, so they were filtered off with celite. The liquids were combined, and were partitioned between dichloromethane and water, and the organics were extracted three times with dichloromethane. The combined organics were washed with brine, dried with sodium sulfate, filtered, and concentrated. The product was chromatographed using a 30% ethyl acetate in heptane solvent solution. 4.10 g of the title product were recovered. (28% yield through first two steps) MS (ESI+) for C11H13NO m/z 176.00 (M+H)+.

Workup

  1. dissolutionhad dissolved
  2. temperatureto cool for 15 minutes
  3. temperatureThe mixture was heated to 130° for 1.5 hours
  4. temperatureThe mixture was cooled in an ice bath
  5. additionadded to the mixture
  6. filtrationwere filtered off with celite
  7. customwere partitioned between dichloromethane and water
  8. extractionthe organics were extracted three times with dichloromethane
  9. washThe combined organics were washed with brine
  10. dry with materialdried with sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe product was chromatographed
  14. custom4.10 g of the title product were recovered

Sources & evidence

ORD record
ord-5238b327dda045779785aae9c0ce0999
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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