Oxalyl chloride → N-(2-methyl-6-quinolyl)-[1-(4-chlorobenzyl)indole-3-yl]glyoxylamide

HRID 902091Notes

Reaction equation

HRID 902091 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].[NH2:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[N:31]=[C:30]([CH3:35])[CH:29]=[CH:28]2>CCOCC.C1COCC1>[CH3:35][C:30]1[CH:29]=[CH:28][C:27]2[C:32](=[CH:33][CH:34]=[C:25]([NH:24][C:18](=[O:22])[C:19]([C:9]3[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[N:7]([CH2:6][C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:17][CH:16]=4)[CH:8]=3)=[O:20])[CH:26]=2)[N:31]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 1031482-Methylquinolin-6-amineHCID 9671631-(4-Chlorobenzyl)-1h-indole

Product 1

HCID 15541793N-(2-methyl-6-quinolyl)-[1-(4-chlorobenzyl)indole-3-yl]glyoxylamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-4 °C

Procedure

At 0° C. and under nitrogen, a solution of 10.2 g (42.2 mmol) of 1-(4-chlorobenzyl)indole in 50 ml of ether is added dropwise to a solution of 5.50 ml of oxalyl chloride in 50 ml of ether. The mixture is heated at reflux for 2 hours and the solvent is then evaporated. 100 ml of tetrahydrofuran were then added to the residue and the solution was cooled to −4° C. and treated dropwise with a solution of 15.66 g (99.0 mmol) of 6-amino-2-methylquinoline in 350 ml of THF. The mixture is heated at reflux for 4 hours and allowed to stand at room temperature overnight. The 6-amino-2-methylquinoline hydrochloride is filtered off with suction, the precipitate is washed with THF, the filtrate is concentrated under reduced pressure and the residue is recrystallized from methyl ethyl ketone/methylene chloride.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2 hours
  3. customthe solvent is then evaporated
  4. addition100 ml of tetrahydrofuran were then added to the residue
  5. temperatureThe mixture is heated
  6. temperatureat reflux for 4 hours
  7. filtrationThe 6-amino-2-methylquinoline hydrochloride is filtered off with suction
  8. washthe precipitate is washed with THF
  9. concentrationthe filtrate is concentrated under reduced pressure
  10. customthe residue is recrystallized from methyl ethyl ketone/methylene chloride

Sources & evidence

ORD record
ord-bcabd13b9fd04b538df7b276c836fccf
Source dataset
uspto-grants-2008_04
Patent number
US07365081B2

Reaction notes

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