Hydrochloric Acid → (5-Amino-1H-benzo[d]imidazol-2-yl)methanol

HRID 1262226Notes

Reaction equation

HRID 1262226 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH2:12][OH:13])[NH:9][C:8]=2[CH:14]=1)([O-])=O.Cl>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH2:12][OH:13])[NH:9][C:8]=2[CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 3744471(5-nitro-1H-1,3-benzodiazol-2-yl)methanol

Product 1

HCID 838521(5-Amino-1H-benzo[d]imidazol-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

(6-Nitro-1H-benzoimidazol-2-yl)-methanol (1.00 g, 5.18 mmol) was dissolved in methanol (50.0 mL) and 3.00 M hydrogen chloride in methanol (8.63 mL, 25.9 mmol). 10% Palladium on Carbon (50% wet) (55.1 mg, 0.0259 mmol) was added and the reaction was hydrogenated at 40 psi. for 3 hours. The reaction was then filtered through celite to remove the catalyst and then concentrated under reduced pressure to obtain (6-Amino-1H-benzoimidazol-2-yl)-methanol; dihydrochloride as a brown foam (1.13 g, 92%). Product is used without further purification.

Workup

  1. filtrationThe reaction was then filtered through celite
  2. customto remove the catalyst
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e37874da161458d83c67c4b7d40e847
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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