Methanol → 1H-Benzimidazol-6-ol,1-methyl-(9CI)

HRID 1777122Notes

Reaction equation

HRID 1777122 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([OH:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.[CH3:13]O>C(O)=O.[Fe]>[CH3:1][N:2]1[C:3]2[CH:4]=[C:5]([OH:12])[CH:6]=[CH:7][C:8]=2[N:9]=[CH:13]1

Participants

5

Reactant 2

HCID 887MethanolHCID 146175Phenol, 3-(methylamino)-4-nitro-

Product 1

HCID 124702491H-Benzimidazol-6-ol,1-methyl-(9CI)

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Fe Powder (4.33 g, 77.4 mmol) was added to a solution of 3-(methylamino)-4-nitrophenol (1.3 g, 7.74 mmol) in HCOOH (30 mL) and the mixture heated to 100° C. for 16 h. After cooling to room temperature, MeOH (250 mL) was added to mixture and filtered over a pad of Celite. The filtrate was collected, concentrated and the residue purified by column chromatography to give the crude desired product (1.2 g) and was used directly in the next step. LCMS (m/z): 149.06 (M+1).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered over a pad of Celite
  3. customThe filtrate was collected
  4. concentrationconcentrated
  5. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-807cf602b7a04150bce395b90636d211
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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