Hydrochloric Acid → 8-Hydroxy-5-[methyl(ethylsulfonyl)amino]-1,6-naphthyridine-7-carboxylic acid

HRID 2252822Notes

Reaction equation

[OH-].[Na+].[OH:3][C:4]1[C:5]([C:21]([O:23]C)=[O:22])=[N:6][C:7]([N:14]([CH3:20])[S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2.Cl>O1CCOCC1.O>[OH:3][C:4]1[C:5]([C:21]([OH:23])=[O:22])=[N:6][C:7]([N:14]([CH3:20])[S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2

Participants

Conditions

Temperature: 55 °C

Procedure

Sodium hydroxide (6.73 mL, 6.73 mmol, 1N solution) was added to a suspension of methyl 8-hydroxy-5-[methyl(ethylsulfonyl)amino]-1,6-naphthyridine-7-carboxylate (730 mg, 2.24 mmol) in a 2:1 solution of dioxane/water (20 mL) and the resulting mixture was heated overnight at 55° C. overnight. The opaque solution was acidified to a pH=7 using 1N HCl solution. The reaction was cooled and the solids that had precipitated out of solution were collected by vacuum filtration to give the desired product as an off-white solid.

Workup

temperatureThe reaction was cooled
customthe solids that had precipitated out of solution
filtrationwere collected by vacuum filtration

Sources & evidence

ORD record: ord-de2cf0103f9c4f75acbd77cd59c68c65
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323460B2

Reaction notes

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