N-Methyl-4-nitrobenzeneethanesulfonamide → 4-Amino-N-methylbenzeneethanesulfonamide

HRID 1190143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190143
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)(=[O:5])=[O:4]>CO.[Pd]>[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)(=[O:4])=[O:5]

Komponenten

4

Edukt 1

HCID 13475730N-Methyl-4-nitrobenzeneethanesulfonamide

Produkt 1

HCID 134757684-Amino-N-methylbenzeneethanesulfonamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 402 mg (1.65 mmol) of 2-(4-nitro-phenyl)-ethanesulfonic acid methylamide (as prepared in the previous step) in MeOH (30 mL) was hydrogenated over 10% Pd/C (Degussa type E101-NE/W, Aldrich, 50% by weight water) at 20 psi of H2 for 19 h. The reaction mixture was filtered through Celite, and the filter cake was washed with MeOH. Solvents were evaporated in vacuo. Silica gel chromatography of the residue on a 25-g Varian MegaBond Elut SPE column with 50% EtOAc-hexane afforded 318 mg (90%) of the title compound as a white solid: 1H-NMR (CD3CN; 400 MHz): δ 7.01 (d, 2H, J=8.4 Hz), 6.61 (d, 2H, J=8.4 Hz), 5.00-4.92 (br s, 1H), 4.12-4.02 (br s, 2H), 3.24-3.17 (m, 2H), 2.92-2.86 (m, 2H), 2.67 (s, 3H, J=5.2 Hz).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH
  3. customSolvents were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bdb16c05c88d4eda9fb9e35434014513
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674100B2

Notizen zur Reaktion

Wird geladen…