[5-(2-morpholin-4-yl-ethoxy)-1H-indol-2-yl]-methanol → 5-(2-morpholin-4-yl-ethoxy)-1H-indole-2-carbaldehyde

HRID 1790901Notes

Reaction equation

HRID 1790901 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([CH2:19][OH:20])=[CH:13]3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>ClCCl.[O-2].[Mn+4].[O-2]>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([CH:19]=[O:20])=[CH:13]3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 22042178[5-(2-morpholin-4-yl-ethoxy)-1H-indol-2-yl]-methanol

Product 1

HCID 220421095-(2-morpholin-4-yl-ethoxy)-1H-indole-2-carbaldehydeYield 25.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese (IV) oxide (3.2 g, 36 mmol) was added to [5-(2-morpholin-4-yl-ethoxy)-1H-indol-2-yl]-methanol (0.7 g) in dichloromethane (150 mL). The mixture was stirred at room temperature for 16 hours. The precipitate was filtered off and the filtrate was concentrated. The residue was recrystallized from ethyl acetate and hexane to give 0.18 g of 5-(2-morpholin-4-yl-ethoxy)-1H-indole-2-carbaldehyde.

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-d303012ec1434d6ba766c694c2310c35
Source dataset
uspto-grants-2006_07
Patent number
US07071332B2

Reaction notes

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