Oxalyl chloride → 5,6-Dimethoxy-2-methyl-3-indoleglyoxylyl chloride

HRID 2071562Notes

Reaction equation

HRID 2071562 reaction equation
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=[O:3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][C:13]([CH3:20])=[CH:12]2>CCOCC>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][C:13]([CH3:20])=[C:12]2[C:1](=[O:5])[C:2]([Cl:4])=[O:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 2665965,6-dimethoxy-2-methyl-1H-indole

Product 1

HCID 131955395,6-Dimethoxy-2-methyl-3-indoleglyoxylyl chloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8.7 g of oxalyl chloride are added dropwise to a stirring solution, cooled to about -10° C., of 12.0 g of 5,6-dimethoxy-2-methylindole in 250 ml of ether. After addition is completed, the mixture is stirred for 10 minutes, producing a bright orange precipitate of 5,6-dimethoxy-2-methyl-3-indole glyoxylyl chloride which is immediately used for the next step.

Workup

  1. additionAfter addition

Sources & evidence

ORD record
ord-c882c8d4174341b1b4ac569dfacca98c
Source dataset
uspto-grants-1977_09
Patent number
US04046900

Reaction notes

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