2-Methyl-5-nitrobenzene-1-sulfonamide → 5-Amino-2-methylbenzenesulfonamide

HRID 454963

Reaktionsgleichung

Reaktionsgleichung von HRID 454963
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][C:10]=1[CH3:11])(=[O:4])=[O:3]>ClCCl.CO.[Pd]>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:10]=1[CH3:11])[NH2:12])(=[O:3])=[O:4]

Komponenten

5

Edukt 1

HCID 2342822-Methyl-5-nitrobenzene-1-sulfonamide

Produkt 1

HCID 2355115-Amino-2-methylbenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-aminosulfonyl-4-methylnitrobenzene in dichloromethane and methanol was added 10% Pd/C and the mixture shaken under a hydrogen atmosphere at 50 psi for 15 minutes. The mixture was filtered through diatomaceous earth and the filter cake was washed with methanol. The combined organic solvents were concentrated under reduced pressure to give crude product, which was further purified by flash column chromatography (ethyl acetate:hexanes 1:1) to give 3-aminosulfonyl-4-methylaniline, LCMS: purity: 87%; MS (m/e): 187 (MH+).

Aufarbeitung

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. washthe filter cake was washed with methanol
  3. concentrationThe combined organic solvents were concentrated under reduced pressure
  4. customto give crude product, which
  5. customwas further purified by flash column chromatography (ethyl acetate:hexanes 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-db99fe3bbabb41c1ad05bb182e7172f2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497279B2

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