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

HRID 1429453Notes

Reaction equation

HRID 1429453 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-f8387e44eabe472babf0e1e7d4c613ee
Source dataset
uspto-grants-2015_01
Patent number
US08940726B2

Reaction notes

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