Ethanol → N-hydroxy-2-[[4-methoxybenzenesulfonyl](2-quinolinylmethyl)amino]acetamide

HRID 1720612

Reaktionsgleichung

Reaktionsgleichung von HRID 1720612
C([O:5][NH:6][C:7](=[O:32])[CH2:8][N:9]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)(=[O:23])=[O:22])[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1)(C)(C)C.C(O)C>C(Cl)Cl>[OH:5][NH:6][C:7](=[O:32])[CH2:8][N:9]([S:21]([C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)(=[O:23])=[O:22])[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1

Komponenten

4

Edukt 2

HCID 702EthanolHCID 22907171N-(t-Butyloxy)-2-[[4-methoxybenzenesulfonyl](2-quinolinylmethyl)amino]acetamide

Produkt 1

HCID 22907131N-hydroxy-2-[[4-methoxybenzenesulfonyl](2-quinolinylmethyl)amino]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-(t-Butyloxy)-2-[[4-methoxybenzenesulfonyl](2-quinolinylmethyl)amino]acetamide (1.15 g, 2.42 mmol) is dissolved in methylene chloride (30.0 mL) and ethanol (0.20 mL) in a glass sealed tube. Hydrochloric acid gas (from a lecture bottle) is bubbled through the solution for 20 minutes, and then the tube is sealed and stands at room temperature overnight. The next day, additional hydrochloric acid gas is bubbled through the solution for 20 minutes, more ethanol (0.20 mL) is added, and then the tube is sealed and stands at room temperature for two days. After that time, the solvent is removed. The product is purified by silica gel chromatography (5% to 15% methanol/methylene chloride with ~1% ammonium hydroxide) to give N-hydroxy-2-[[4-methoxybenzenesulfonyl](2-quinolinylmethyl)amino]acetamide, m.p. 177°-178° C.

Aufarbeitung

  1. customHydrochloric acid gas (from a lecture bottle) is bubbled through the solution for 20 minutes
  2. customthe tube is sealed
  3. customThe next day, additional hydrochloric acid gas is bubbled through the solution for 20 minutes
  4. additionmore ethanol (0.20 mL) is added
  5. customthe tube is sealed
  6. waitstands at room temperature for two days
  7. customAfter that time, the solvent is removed
  8. customThe product is purified by silica gel chromatography (5% to 15% methanol/methylene chloride with ~1% ammonium hydroxide)

Quellen und Nachweise

ORD-Eintrag
ord-c405b43fa55c429b9198e555f3e339ba
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506242

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