Hydrochloric Acid → 8-(3,3-Dimethylpiperidin-1-yl)-9-fluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylic acid

HRID 413053Notes

Reaction equation

[OH-].[K+].[CH3:3][C:4]1([CH3:32])[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[C:30]([F:31])=[CH:29][C:13]3[C:14]4[C:15](=[O:28])[C:16]([C:23]([O:25]CC)=[O:24])=[CH:17][N:18]([CH3:22])[C:19]=4[CH:20]=[N:21][C:12]=3[CH:11]=2)[CH2:5]1.Cl>C(O)C.O>[CH3:3][C:4]1([CH3:32])[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[C:30]([F:31])=[CH:29][C:13]3[C:14]4[C:15](=[O:28])[C:16]([C:23]([OH:25])=[O:24])=[CH:17][N:18]([CH3:22])[C:19]=4[CH:20]=[N:21][C:12]=3[CH:11]=2)[CH2:5]1

Participants

Conditions

Temperature: 100 °C

Procedure

1.4 cm3 of 1 N aqueous potassium hydroxide was added, with stirring, to a suspension of 0.5 g of ethyl 8-(3,3-dimethylpiperidin-1-yl)-9-fluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylate in 15 cm3 of ethanol and 15 cm3 of water. The mixture was heated at about 100° C. for one hour. The suspension obtained was acidified by addition of 1.4 cm3 of 1 N aqueous hydrochloric acid. After cooling, the precipitate was dewatered, washed three times with 10 cm3 of water, three times with 10 cm3 of ethanol, and three times with 10 cm3 of ether. The solid was dried at about 80° C. at 1 kPa for 4 hours. 0.38 g of 8-(3,3-dimethylpiperidin-1-yl)-9-fluoro-4-methyl-1-oxo-1,4-dihydrobenzo[f][1,7]naphthyridine-2-carboxylic acid was obtained in the form of a yellow solid, which melted with decomposition at about 286-7° C.

Workup

customThe suspension obtained
temperatureAfter cooling
washwashed three times with 10 cm3 of water, three times with 10 cm3 of ethanol, and three times with 10 cm3 of ether
customThe solid was dried at about 80° C. at 1 kPa for 4 hours

Sources & evidence

ORD record: ord-de6694b2b6444410a3428f71c4c27320
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566362B2

Reaction notes

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