2-(hydroxymethyl)-1H-indole-5-carbonitrile → 2-formyl-1H-indole-5-carbonitrile

HRID 1512742Notes

Reaction equation

HRID 1512742 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]#[N:13])=[CH:7][CH:6]=2>ClCCl.O=[Mn]=O>[CH:2]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]#[N:13])=[CH:7][CH:6]=2)=[O:1]

Participants

4

Reactant 1

HCID 135679562-(hydroxymethyl)-1H-indole-5-carbonitrile

Product 1

HCID 115791932-formyl-1H-indole-5-carbonitrileYield 80.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

MnO2 (1.76 g) was added to a solution of 2-(hydroxymethyl)-1H-indole-5-carbonitrile (D24) (290 mg) in dichloromethane (100 mL) at RT. The reaction mixture was stirred at RT for 1 hour. The solid was filtered off and washed with dichloromethane. The filtrate was concentrated to afford 2-formyl-1H-indole-5-carbonitrile (D28) (230 mg) as a white solid. MS (ES): C10H6N2O requires 170; found 169.1 (M−H+).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3ba200123d094626990593699608c7bf
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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