1-Methyl-6-nitrobenzimidazole → 1-Methyl-1H-benzimidazol-6-amine

HRID 2375918Notes

Reaction equation

HRID 2375918 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1>C(O)C.[Pd]>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([NH2:11])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1

Participants

4

Reactant 1

HCID 949781-Methyl-6-nitrobenzimidazole

Product 1

HCID 136802831-Methyl-1H-benzimidazol-6-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd/C (17 mg, 10%, with 50% water) was added into the suspension of 1-methyl-6-nitro-1H-1,3-benzimidazole (85.0 mg, 0.480 mmol) in ethanol (3 mL). The mixture was degassed and filled with H2. The mixture was stirred at rt under balloon pressure for 16 h. After that time, the mixture was filtered and concentrated in vacuo to obtain the title compound as pink crystals. 1H NMR (CD3OD, 400 MHz): δ=3.67 (s, 3H), 6.69-6.73 (m, 2H), 7.33 (dd, 1H, J=0.4 & 8.8 Hz), 7.77 (s, 1H). MS (ES+): m/z 148.16 (100) [MH+]. HPLC: tR=0.43 min (ZQ2000, polar—5 min).

Workup

  1. customThe mixture was degassed
  2. additionfilled with H2
  3. filtrationAfter that time, the mixture was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76e625f5be39408db0d54e25744bb982
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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