Chloroform → HCID 57815494, compound

HRID 385605Notes

Reaction equation

HRID 385605 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:19].C(Cl)(Cl)Cl>C(C(C)=O)C.Cl>[O:19]=[C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:11][N:10]=2)[N:5]1[CH2:4][CH:3]=[O:2]

Participants

5

Reactant 2

HCID 6212ChloroformHCID 57815363HCID 57815363, compound

Product 1

HCID 57815494HCID 57815494, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 90 mg of 1-(2,2-dimethoxyethyl)-7-(trifluoromethyl)-1,5-naphthyridin-2(1H)-one in 0.72 mL of methyl ethyl ketone, 38 μL of concentrated hydrochloric acid was added, and the mixture was heated under reflux while stirring for 1 hour 30 minutes. The reaction mixture was cooled to room temperature, thereto were added chloroform and a saturated aqueous sodium hydrogen carbonate solution, the organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 67 mg of (2-oxo-7-(trifluoromethyl)-1,5-naphthyridin-1(2H)-yl)acetaldehyde as a brown oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customa saturated aqueous sodium hydrogen carbonate solution, the organic layer was separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3b567e6170e349faae766ef481dcba66
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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