1-Methylindole → (1-methyl-1H-indol-3-yl)-oxo-acetyl chloride

HRID 579253Notes

Reaction equation

HRID 579253 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[C:11](Cl)(=[O:15])[C:12]([Cl:14])=[O:13]>C(OCC)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=[O:15])[C:12]([Cl:14])=[O:13])=[CH:3]1

Participants

4

Reactant 2

HCID 117811-MethylindoleHCID 65578Oxalyl chloride

Product 1

HCID 10799027(1-methyl-1H-indol-3-yl)-oxo-acetyl chlorideYield 72.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 100 ml volume three-necked flask, N-methylindole (5.0 g) and diethylether (35 ml) were added under a nitrogen atmosphere, and added oxalyl chloride (9.7 g) at less than 5° C. The mixture was stirred under ice-cooling for 3 hours, and the precipitated solids were collected by auction filtration, washed with cold diethylether, and dried under reduced pressure to give 6.1 g of 2-(1-methyl-1H-indol-3-yl)-2-oxoacetyl chloride (26-a).

Workup

  1. temperaturecooling for 3 hours
  2. filtrationthe precipitated solids were collected by auction filtration
  3. washwashed with cold diethylether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b45bf099fb2642b09c0b8d6d3dd68eab
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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