Hydrochloric Acid → HCID 22716700, compound

HRID 1582994Notes

Reaction equation

HRID 1582994 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([C:7]1[C:8]([NH:14][CH2:15][CH3:16])=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)=O.[C:20]1(=[O:27])[O:26][C:24](=[O:25])[CH2:23][CH2:22][CH2:21]1.Cl>O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[C:7]3[C:8](=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=3)[N:14]([CH2:15][CH3:16])[C:24](=[O:25])[C:23]=2[CH2:22][CH2:21][C:20]([OH:26])=[O:27])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7940Glutaric anhydrideHCID 11809320HCID 11809320, compound

Product 1

HCID 22716700HCID 22716700, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1.2 g of 3-(3-bromobenzoyl)-2-ethylamino-6-methylpyridine and 2.1 g of glutaric anhydride was stirred under heating at 150° C. for 15 hours. After cooling to room temperature, 10 ml of 1M hydrochloric acid was added thereto and the whole was heated under reflux for 1 hour. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and then the solvent was evaporated. To the residue was added 50 ml of ethanol and 0.5 ml of concentrated sulfuric acid, followed by heating under reflux for 1 hour. The reaction mixture was cooled to room temperature, diluted with water and then extracted with ethyl acetate. The organic layer was washed with saturated brine and then the solvent was evaporated. The residue was purified by a silica gel column chromatography (chloroform). Thereafter, similar operations to those in Example 2 were carried out to obtain 1.00 g of 3-[4-(3-bromophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid as pale yellow crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperaturethe whole was heated
  3. temperatureunder reflux for 1 hour
  4. temperatureAfter cooling to room temperature
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. customthe solvent was evaporated
  8. additionTo the residue was added 50 ml of ethanol and 0.5 ml of concentrated sulfuric acid
  9. temperatureby heating
  10. temperatureunder reflux for 1 hour
  11. temperatureThe reaction mixture was cooled to room temperature
  12. additiondiluted with water
  13. extractionextracted with ethyl acetate
  14. washThe organic layer was washed with saturated brine
  15. customthe solvent was evaporated
  16. customThe residue was purified by a silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-fbd49979d4184820a44eb8040ceefe59
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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