HCID 86694693, compound → HCID 86694694, compound

HRID 475098Notes

Reaction equation

HRID 475098 reaction equation
[CH2:1]([C:3]1[C:11]2[N:10]=[CH:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]=2[CH:6]=[CH:5][C:4]=1[N+:19]([O-])=O)[CH3:2]>CO.[Pd]>[NH2:19][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH:9]=[N:10][C:11]=2[C:3]=1[CH2:1][CH3:2]

Participants

4

Reactant 1

HCID 86694693HCID 86694693, compound

Product 1

HCID 86694694HCID 86694694, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-ethyl-5-nitro-1H-benzo[d]imidazole-1-carboxylate (20.0 g, 0.07 mol) in dry MeOH (500 mL) was added Pd/C (1.5 g). The suspension was then stirred under hydrogen (3 kg pressure) for 6 h. After completion, the reaction mixture was filtered through a celite pad and concentrated to give tert-butyl 5-amino-4-ethyl-1H-benzo[d]imidazole-1-carboxylate (13.6 g, 76% yield). The crude product was used for the next step without further purification.

Workup

  1. filtrationAfter completion, the reaction mixture was filtered through a celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d81c39cb054d4250a1a008cf902bb767
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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