Hydrochloric Acid → (7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde hydrochloride monohydrate

HRID 1804734Notes

Reaction equation

[ClH:1].C([O:4][CH:5](OCC)[CH2:6][N:7]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=2)[CH:10]=[CH:9][C:8]1=[O:18])C>CC(=O)CC>[OH2:4].[ClH:1].[F:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[CH:9][C:8](=[O:18])[N:7]2[CH2:6][CH:5]=[O:4])=[N:12][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To 480 mL of 2-butanone, 30 mL of 12 mol/L hydrochloric acid was added, the mixture was heated to 70° C. and a solution of 60 g of 1-(2,2-diethoxyethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one in 60 mL of 2-butanone was added dropwise, followed by reflux for 2 hours. After cooling the reaction mixture to 25° C., the solid product was obtained by filtration and washed with 2-butanone to give 50.3 g of (7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde hydrochloride monohydrate as a light yellow solid.

Workup

temperatureby reflux for 2 hours
temperatureAfter cooling the reaction mixture to 25° C.
customthe solid product was obtained by filtration
washwashed with 2-butanone

Sources & evidence

ORD record: ord-3cc5b2d1bf004bb38fc44325f47b7c8e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354426B2

Reaction notes

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