Dichloromethane → (6-cyano-1-methyl-1H-indol-3-yl)glyoxylyl chloride

HRID 651772Notes

Reaction equation

HRID 651772 reaction equation
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=[O:3].C(Cl)Cl.[C:10]([C:12]1[CH:20]=[C:19]2[C:15]([CH:16]=[CH:17][N:18]2[CH3:21])=[CH:14][CH:13]=1)#[N:11]>CCOCC>[C:10]([C:12]1[CH:20]=[C:19]2[C:15]([C:16]([C:1](=[O:5])[C:2]([Cl:4])=[O:3])=[CH:17][N:18]2[CH3:21])=[CH:14][CH:13]=1)#[N:11]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chloride2×HCID 153844931-Methyl-1H-indole-6-carbonitrile

Product 1

HCID 15384492(6-cyano-1-methyl-1H-indol-3-yl)glyoxylyl chlorideYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of oxalyl chloride in CH2Cl2 (2 M, 1.6 mL, 3.2 mmol) was added dropwise to a solution of 6-cyano-1-methyl-1H-indole (360 mg, 2.3 mmol) in ether (5 mL). Stirring was continued for 30 min at 0° C. and the cooling bath was removed. After 2 h, more of the 2 M solution of oxalyl chloride (0.2 mL, 0.4 mmol.) was added. Stirring was continued at room temperature for additional 2 h. The solid was filtered and washed with ether to give (6-cyano-1-methyl-1H-indol-3-yl)glyoxylyl chloride (450 mg, 79%). Ref:: Troxler, F.; Hamisch, A.; Bormann, G.; Seemann, F.; Szabo, L.; Helv. Chim Acta, 1968, 51(1), 1616.

Workup

  1. customthe cooling bath was removed
  2. waitAfter 2 h
  3. stirringStirring
  4. waitwas continued at room temperature for additional 2 h
  5. filtrationThe solid was filtered
  6. washwashed with ether

Sources & evidence

ORD record
ord-bb205e19602e4178acd79c4b71720d07
Source dataset
uspto-grants-2001_08
Patent number
US06281356B1

Reaction notes

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