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

HRID 1804722Notes

Reaction equation

C[O:2][CH:3](OC)[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([F:15])[CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:16].[ClH:19]>CC(=O)CC>[OH2:2].[ClH:19].[F:15][C:12]1[CH:13]=[C:14]2[C:9]([CH:8]=[CH:7][C:6](=[O:16])[N:5]2[CH2:4][CH:3]=[O:2])=[N:10][CH:11]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To a suspension of 158 g of 1-(2,2-dimethoxyethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one in 1.26 L of 2-butanone, 79 mL of 12 mol/L hydrochloric acid was added at room temperature, and the mixture was refluxed for 3 hours. After cooling the reaction mixture to 10° C., the solid product was obtained by filtration and washed with 2-butanone to give 152 g of (7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde hydrochloride monohydrate as a light yellow solid.

Workup

additionwas added at room temperature
temperaturethe mixture was refluxed for 3 hours
customthe solid product was obtained by filtration
washwashed with 2-butanone

Sources & evidence

ORD record: ord-bc19818b192d44109b1d8e962a116cab
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354426B2

Reaction notes

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