Hydrochloric Acid → 7-Bromo-9-cyclopropyl-6-fluoro-9H-isothiazolo[5,4-B]quinoline-3,4-dione

HRID 1640943Notes

Reaction equation

HRID 1640943 reaction equation
C([O-])(O)=O.[Na+].[NH2:6]OS(O)(=O)=O.C([O:14][C:15]([C:17]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][C:22]([Br:29])=[C:23]([F:28])[CH:24]=2)[N:19]([CH:30]2[CH2:32][CH2:31]2)[C:18]=1[SH:33])=O)C.Cl>C1COCC1>[Br:29][C:22]1[CH:21]=[C:20]2[C:25]([C:26](=[O:27])[C:17]3[C:15](=[O:14])[NH:6][S:33][C:18]=3[N:19]2[CH:30]2[CH2:32][CH2:31]2)=[CH:24][C:23]=1[F:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76284hydroxylamine-O-sulfonic acidHCID 516892Sodium BicarbonateHCID 178470118HCID 178470118, compound

Product 1

HCID 599995297-Bromo-9-cyclopropyl-6-fluoro-9H-isothiazolo[5,4-B]quinoline-3,4-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of NaHCO3 solution (51 mg, 0.9 ml water) and hydroxylamine-O-sulfonic acid (27 mg, 0.24 mmole, 4.2 equiv.) is added to a stirred solution of 7-Bromo-1-cyclopropyl-6-fluoro-2-mercapto-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (6, 22 mg, 0.057 mmole) in THF (0.7 ml). The reaction mixture is stirred at room temperature for approximately 3 hours until the reaction is complete. The reaction mixture is acidified by the addition of 0.5N HCl and filtered. The resulting solid is washed with water (3×) and dried yielding 7 as a white solid. 1H NMR (DMSO-d6) δ: 8.39 (d, 1H), 8.06 (d, 1H), 3.63 (m, 1H), 1.41 (m, 2H), 1.26 (m, 2H). 19F NMR (DMSO-d6) δ: 114.9 (s, 1H).

Workup

  1. filtrationfiltered
  2. washThe resulting solid is washed with water (3×)
  3. customdried

Sources & evidence

ORD record
ord-4bba65ea41064423ad1d161cd9efddd6
Source dataset
uspto-grants-2012_02
Patent number
US08114888B2

Reaction notes

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