8-(1,1-Dioxo-2H-naphtho[1,8-cd]isothiazol-2-yl)-octanoic acid benzyloxyamide → 8-(1,1-dioxo-2H-naphtho[1,8-cd]isothiazol-2-yl)-octanoic acid hydroxyamide

HRID 9083Notes

Reaction equation

HRID 9083 reaction equation
C([O:8][NH:9][C:10](=[O:32])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[CH:27]=[CH:28][CH:29]=[C:20]([C:21]=23)[S:19]1(=[O:31])=[O:30])C1C=CC=CC=1>CO.[Pd]>[OH:8][NH:9][C:10](=[O:32])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[CH:27]=[CH:28][CH:29]=[C:20]([C:21]=23)[S:19]1(=[O:31])=[O:30]

Participants

4

Reactant 1

HCID 865918808-(1,1-Dioxo-2H-naphtho[1,8-cd]isothiazol-2-yl)-octanoic acid benzyloxyamide

Product 1

HCID 102921288-(1,1-dioxo-2H-naphtho[1,8-cd]isothiazol-2-yl)-octanoic acid hydroxyamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-(1,1-Dioxo-2H-naphtho[1,8-cd]isothiazol-2-yl)-octanoic acid benzyloxyamide (0.47 g) in methanol (30 ml) was hydrogenated for 1.5 h in the presence of palladium on barium sulfate at ambient temperature and pressure. The catalyst was removed by filtration and the solvent was evaporated. The residue was purified by column chromatography (silica gel; ethyl acetate as eluent). There was thus obtained 8-(1,1-dioxo-2H-naphtho[1,8-cd]isothiazol-2-yl)-octanoic acid hydroxyamide (61%) as a colorless oil. MS: 363 (M+H+).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. customThe residue was purified by column chromatography (silica gel; ethyl acetate as eluent)

Sources & evidence

ORD record
ord-2b702c2e3f184302b8ebff254e729685
Source dataset
uspto-grants-2006_08
Patent number
US07091229B2

Reaction notes

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