Hydrochloric Acid → HCID 22106115, compound

HRID 1456408Notes

Reaction equation

HRID 1456408 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:4]([C:19]([O:21]CC)=[O:20])[C:3]1=[O:24].[OH-].[Na+].Cl>C(O)C.O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[C:4]([C:19]([OH:21])=[O:20])[C:3]1=[O:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22105930HCID 22105930, compound

Product 1

HCID 22106115HCID 22106115, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 1-methyl-4-(2-chlorophenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylate (4.6 g, 13.4 mmol) in ethanol (20 ml) was added sodium hydroxide (2.1 g, 52.5 mmol), and the mixture was refluxed for 0.5 hour. The mixture was diluted with water, and the pH value thereof was adjusted to pH 4 with 2N aqueous hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The precipitated crystals were recrystallized from ethyl acetate to give the title compound (3.52 g, 11.2 mmol) as a colorless crystal.

Workup

  1. temperaturethe mixture was refluxed for 0.5 hour
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe precipitated crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-31a5ffc9607c4c69aa78bfdf005f0e06
Source dataset
uspto-grants-1998_12
Patent number
US05843957

Reaction notes

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