Oxalyl chloride → HCID 15458808, compound

HRID 1004203Notes

Reaction equation

HRID 1004203 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[CH:4]=[CH:3]1.[C:14](Cl)(=[O:18])[C:15]([Cl:17])=[O:16]>CCOCC>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[C:4]([C:14](=[O:18])[C:15]([Cl:17])=[O:16])=[CH:3]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 106073591-Methyl-6-nitro-1H-indole

Product 1

HCID 15458808HCID 15458808, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.33 g (7.55 mmol) of 1-methyl-6-nitro-1H-indole (2) in 40 ml of ether were added 1.5 ml (17.2 mmol) of oxalyl chloride at 0-5° C. under Argon. A precipitate was formed. After 3 hours stirring, the resulting solid was filtered, washed with a small amount of ether and dried to yield 1.9 g (95%) of (1-methyl-6-nitro-1H-indol-3-yl)-oxo-acetyl chloride (3) as a yellow solid. This material was used without purification.

Workup

  1. customA precipitate was formed
  2. filtrationthe resulting solid was filtered
  3. washwashed with a small amount of ether
  4. customdried

Sources & evidence

ORD record
ord-97f46576e6d742b89638665d1447b418
Source dataset
uspto-grants-2000_04
Patent number
US06048887

Reaction notes

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