Oxalyl chloride → N-(6,7-Methylenedioxyquinolin-4-yl)-N-[2-(N,N-dimethylamino)--methylethyl)-2-iodo-4,5-dimethoxybenzamide

HRID 505876Notes

Reaction equation

HRID 505876 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([NH:14][CH:15]([CH3:20])[CH2:16][N:17]([CH3:19])[CH3:18])=[CH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1.C(Cl)(=O)[C:22](Cl)=[O:23].[I:27][C:28]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[C:29]=1C(O)=O.[K+].[Br-]>>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([N:14]([CH:15]([CH3:20])[CH2:16][N:17]([CH3:19])[CH3:18])[C:22](=[O:23])[C:36]4[CH:35]=[C:34]([O:37][CH3:38])[C:33]([O:39][CH3:40])=[CH:29][C:28]=4[I:27])=[CH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 253877Potassium BromideHCID 106625572-Iodo-5,6-dimethoxybenzoic acidHCID 22139515N'-(6,7-Methylenedioxyquinolin-4-yl)-N,N-dimethylpropane-1,2-diamine

Product 1

HCID 22139524N-(6,7-Methylenedioxyquinolin-4-yl)-N-[2-(N,N-dimethylamino)--methylethyl)-2-iodo-4,5-dimethoxybenzamideYield 60.4%

Procedure

Prepared from N′-(6,7-Methylenedioxyquinolin-4-yl)-N,N-dimethylpropane-1,2-diamine (273 mg, 1.0 mol) in 60.4% yield with a reaction time of 12 h, from the acid chloride prepared using 4.8 mmol of oxalyl chloride and 1.2 mmol of 2-iodo-5,6-dimethoxybenzoic acid. Compound 7b had: mp 82-84° C.; IR (KBr) 1648, 3415; HRMS calcd for C24H261N3O5H 564.0917; found 564.0997

Workup

  1. customprepared

Sources & evidence

ORD record
ord-5241f28bf1f2412e8d02fc188ff913f2
Source dataset
uspto-grants-2010_08
Patent number
US07781587B2

Reaction notes

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