5-(2-Methylmorpholino)-2-nitroaniline → 4-(2-Methylmorpholino)benzene-1,2-diamine

HRID 1047570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047570
[CH3:1][CH:2]1[CH2:7][N:6]([C:8]2[CH:9]=[CH:10][C:11]([N+:15]([O-])=O)=[C:12]([CH:14]=2)[NH2:13])[CH2:5][CH2:4][O:3]1.[H][H]>C(O)C.[Pd]>[CH3:1][CH:2]1[CH2:7][N:6]([C:8]2[CH:14]=[C:12]([NH2:13])[C:11]([NH2:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][O:3]1

Komponenten

5

Edukt 2

HCID 683849655-(2-Methylmorpholino)-2-nitroanilineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 683850274-(2-Methylmorpholino)benzene-1,2-diamineAusbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

5-(2-Methylmorpholino)-2-nitroaniline (200 mg, 0.843 mmol) was added to the 10% Pd/C (25 mg) in ethanol (25 mL) and then hydrogen gas (60 psi) was applied for overnight at room temperature. The reaction mixture was filtered through Celite, and the solvent was removed in vacuo. Purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound (150 mg). 1H NMR: (400 MHz, DMSO-d6): δ 6.38 (d, 1H, J=8.0 Hz), 6.18 (d, 1H, J=2.4 Hz), 5.99 (dd, 1H, J=2.8 and 8.0 Hz), 4.34 (bs, 2H), 3.96 (bs, 2H), 3.82 (m, 1H), 3.57 (m, 2H), 3.19 (d, 1H, J=11.2 Hz), 3.11 (d, 1H, J=11.2 Hz), 2.44 (m, 1H), 2.13 (t, 1H, J=11.2 Hz), 1.08 (d, 3H, J=6.4 Hz).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed in vacuo
  3. customPurification by flash chromatography (5% CH3OH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-a886b3a13f8e4764a3ed840d6978e756
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569511B2

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