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

HRID 1613165Notes

Reaction equation

HRID 1613165 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.[O:11]=[C:12](Cl)[C:13]([Cl:15])=[O:14]>CCOCC>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:12](=[O:11])[C:13]([Cl:15])=[O:14])=[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 92.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Methylindole (6.8 g; 52.5 mmol) was dissolved in 100 ml of ether. The solution was stirred under a nitrogen atmosphere while α-oxo-α-chloroacetyl chloride (7.6 g; 60.3 mmol) was added in approximately 0.5 ml aliquots via a syringe. The reaction mixture was stirred for an additional 30 minutes at ambient temperature and then cooled in an ice bath. The product was collected as a precipitate on a sintered funnel and dried to yield 10.8 g (48.7 mmol) of 1-methyl α-oxo-3-indoleacetyl chloride, m.p. 122°-133° C.

Workup

  1. additionwas added in approximately 0.5 ml aliquots via a syringe
  2. temperaturecooled in an ice bath
  3. customThe product was collected as a precipitate on a sintered funnel
  4. customdried

Sources & evidence

ORD record
ord-80448fb0207244b4ae8691cde18edcb4
Source dataset
uspto-grants-1993_03
Patent number
US05192770

Reaction notes

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