1-methyl-5-nitro-1H-benzo[d]imidazole → 1-methyl-1H-1,3-benzodiazol-5-amine

HRID 2042111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042111
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N+:11]([O-])=O)=[CH:10][C:5]=2[N:4]=[CH:3]1>CCO.[Pd]>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[N:4]=[CH:3]1

Komponenten

4

Edukt 1

HCID 961731-methyl-5-nitro-1H-benzo[d]imidazole

Produkt 1

HCID 3154991-methyl-1H-1,3-benzodiazol-5-amineAusbeute 108 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

1-Methyl-5-nitro-1H-benzo[d]imidazole (prepared as described in WO 2005/092899; 1.14 g, 6.43 mmol) in EtOH (50 ml) was stirred under H2 (1 atm) at RT in the presence of 10% Pd/C (50 wt % H2O, 1.37 g, 0.643 mmol). After 18 h, the completed reaction was filtered on Celite, rinsing forward with EtOH. The combined filtrates were concentrated to afford crude 1-methyl-1H-benzo[d]imidazol-5-amine (1.02 g, 108% yield) as a dark orange oil which was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6) δ 7.87 (s, 1H), 7.17 (d, J=8.4 Hz, 1H), 6.75 (d, J=2.0 Hz, 1H), 6.59 (dd, J=2.0 and 8.4 Hz, 1H), 4.73 (brs, 2H), 3.69 (s, 3H); MS (ESI) m/z: 148.0 (M+H+).

Aufarbeitung

  1. customthe completed reaction
  2. filtrationwas filtered on Celite
  3. washrinsing forward with EtOH
  4. concentrationThe combined filtrates were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-06adb5e755f140ab9db19e7314e7fd58
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586565B2

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