Indole → 3-Indoleglyoxylyl chloride

HRID 1165081Notes

Reaction equation

HRID 1165081 reaction equation
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=[O:3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1>CCOCC>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:1](=[O:5])[C:2]([Cl:4])=[O:3])=[CH:8]1

Participants

4

Reactant 2

HCID 798IndoleHCID 65578Oxalyl chloride

Product 1

HCID 899523-Indoleglyoxylyl chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Oxalyl chloride (10 ml) was slowly added to a stirred solution of 11.7 g of indole in 50 ml of anhydrous ether at 0° C. The temperature was allowed to reach room temperature and the mixture stirred for a further 2 hours. The orange precipitate was filtered off, washed with anhydrous ether and dried at 50° C. to give 3-indolylglyoxylyl chloride.

Workup

  1. customto reach room temperature
  2. filtrationThe orange precipitate was filtered off
  3. washwashed with anhydrous ether
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-26f928d4f7c841e3a28231e294c5ec03
Source dataset
uspto-grants-1990_03
Patent number
US04906755

Reaction notes

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