2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazol-1-ol → 2,3-Dihydropyrrolo[1,2-a]benzimidazol-1-one

HRID 22290Notes

Reaction equation

HRID 22290 reaction equation
[OH:1][CH:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[CH2:4][CH2:3]1>C(Cl)Cl.C(OCC)(=O)C>[O:1]=[C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 199278092,3-dihydro-1H-pyrrolo[1,2-a]benzimidazol-1-ol

Product 1

HCID 50580322,3-Dihydropyrrolo[1,2-a]benzimidazol-1-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,3-dihydro-1-hydroxy-1H-pyrrolo-[1,2-a]benzimidazole (1.0 g, 5.75 mmol)) in methylene chloride was treated with mangenese dioxide (5 g, 58 mmol) at r.t. and stirred for 10 hour. The mixture was diluted with ethyl acetate and filtered through diatomaceous earth (Celite (trademark)). The filtrate was concentrated and purified to give the title compound. 1HNMR (CDCl3)δ 3.28 (t, 2H), 4.48 (t, 2H), 7.3-7.45 (m, 2H), 7.45-7.55 (m, 1H), 7.86-7.94 (m, 1H) ppm.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite (trademark))
  2. concentrationThe filtrate was concentrated
  3. custompurified

Sources & evidence

ORD record
ord-82cb599521bc42b6af01acc980576057
Source dataset
uspto-grants-1995_06
Patent number
US05428043

Reaction notes

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