(5,6-dichloro-1H-indol-2-yl)methanol → 5,6-dichloro-1H-indole-2-carbaldehyde

HRID 1070694Notes

Reaction equation

HRID 1070694 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([CH2:12][OH:13])=[CH:5]2>C(OCC)C.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([CH:12]=[O:13])=[CH:5]2

Participants

4

Reactant 1

HCID 22397554(5,6-dichloro-1H-indol-2-yl)methanol

Product 1

HCID 108462775,6-dichloro-1H-indole-2-carbaldehydeYield 90.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 5,6-dichloroindole-2-methanol (43 g, 199 mmol) in diethyl ether (1.3 l) was treated with activated MnO2 (64 g, 730 mmol) and stirred for 15 hours at room temperature. Additional MnO2 (20 g, 230 mmol) was added and stirring continued for 5 h. The suspension was filtered on a Celite pad, then the pad was washed with diethyl ether and warm acetone. The pooled organic phases were concentrated to give 38.5 g of the title compound (180 mmol, yield 90.4%) that was used as such in the next step, m.p.=207-208° C.

Workup

  1. stirringstirring
  2. waitcontinued for 5 h
  3. filtrationThe suspension was filtered on a Celite pad
  4. washthe pad was washed with diethyl ether
  5. temperaturewarm acetone
  6. concentrationThe pooled organic phases were concentrated

Sources & evidence

ORD record
ord-d541b3ef956e44dcb99d55482b61dea7
Source dataset
uspto-grants-2005_06
Patent number
US06903117B2

Reaction notes

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