HCID 57815183, compound → HCID 57815306, compound
Reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:14]2[C:9](=[N:10][C:11]([CH3:16])=[C:12]([F:15])[CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:17]>C(C(C)=O)C.Cl>[F:15][C:12]1[CH:13]=[C:14]2[C:9]([CH:8]=[CH:7][C:6](=[O:17])[N:5]2[CH2:4][CH:3]=[O:2])=[N:10][C:11]=1[CH3:16]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 74 °C
Procedure
To a solution of 0.69 g of 1-(2,2-dimethoxyethyl)-7-fluoro-6-methyl-1,5-naphthyridin-2(1H)-one in 6 mL of methyl ethyl ketone, 0.35 mL of concentrated hydrochloric acid was added, and the temperature was increased to 74° C., and the mixture was stirred for 2 hours 50 minutes. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. To the resultant residue, ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate to obtain 0.52 g of (7-fluoro-6-methyl-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde as a light yellow solid.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- distillationthe solvent was distilled off under reduced pressure
- additionTo the resultant residue, ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution were added
- customthe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
Sources & evidence
- ORD record
- ord-3b0df260123c42f6a2bef73c04a43ed3
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367831B2
Reaction notes
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