Sulfuric Acid → HCID 12991190, compound

HRID 1582983Notes

Reaction equation

HRID 1582983 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[CH2:22][CH2:23][C:24](O)=[O:25])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[N:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]([CH2:19][CH3:20])[C:10](=[O:21])[C:9]=2[CH2:22][CH2:23][CH2:24][OH:25])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 10156040337357-62-7

Product 1

HCID 12991190HCID 12991190, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.00 g of 3-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid, 20 ml of methanol and 0.5 ml of concentrated sulfuric acid was heated under reflux for a whole day and night. After cooling to room temperature, saturated sodium bicarbonate aqueous solution was added thereto and the whole was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and then the solvent was evaporated. The residue was purified by a silica gel column chromatography (hexane-ethyl acetate). The resulting compound was dissolved in 20 ml of THF and 500 mg of sodium borohydride was added thereto. While heating under reflux, 3 ml of methanol was added dropwise thereto, and the mixture was further heated under reflux for 3 hours. After cooling to room temperature, 1M hydrochloric acid was added and the whole was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and then the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate) and then recrystallized from diisopropyl ether to obtain 497 mg of 4-(3-chlorophenyl)-1-ethyl-3-(3-hydroxypropyl)-7-methyl-1,8-naphthyridin-2(1H)-one as colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a whole day and night
  3. extractionthe whole was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by a silica gel column chromatography (hexane-ethyl acetate)
  7. dissolutionThe resulting compound was dissolved in 20 ml of THF
  8. addition500 mg of sodium borohydride was added
  9. temperatureWhile heating
  10. temperatureunder reflux
  11. addition3 ml of methanol was added dropwise
  12. temperaturethe mixture was further heated
  13. temperatureunder reflux for 3 hours
  14. temperatureAfter cooling to room temperature
  15. addition1M hydrochloric acid was added
  16. extractionthe whole was extracted with ethyl acetate
  17. washThe organic layer was washed with water and saturated brine
  18. customthe solvent was evaporated
  19. customThe resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate)
  20. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-132e5b3b9d3f49e9a915a4ed6cf4dd50
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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