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

HRID 505875Notes

Reaction equation

HRID 505875 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([NH:14][CH2:15][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:21](Cl)=[O:22].[I:26][C:27]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[C:28]=1C(O)=O>>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([N:14]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:21](=[O:22])[C:35]4[CH:34]=[C:33]([O:36][CH3:37])[C:32]([O:38][CH3:39])=[CH:28][C:27]=4[I:26])=[CH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 106625572-Iodo-5,6-dimethoxybenzoic acidHCID 10923240N'-(6,7-Methylenedioxyquinolin-4-yl)-N,N-dimethylethane-1,2-diamine

Product 1

HCID 66629643N-(6,7-Methylenedioxyquinolin-4-yl)-N-(N,N-dimethylaminoethyl)-2-iodo-4,5-dimethoxybenzamideYield 71%

Procedure

Prepared from N′-(6,7-Methylenedioxyquinolin-4-yl)-N,N-dimethylethane-1,2-diamine (1.0 g, 3.84 mmol) in 71% yield with a reaction time of 3 h, from the acid chloride prepared using 10 mmol of oxalyl chloride and 4.8 mmol of 2-iodo-5,6-dimethoxybenzoic acid. Compound 7a had: IR(CHCl3) 1652; 1H NMR (CDCl3) δ 2.74 (s, 6H), 2.66 (t, 2.H, J=7.0), 3.33 (s, 3H), 3.74 (s, 3H), 3.96 (m, 1H), 4.49, (m, 1H), 6.15 (s, 2H), 6.41 (s, 1H), 7.03 (s, 1H), 7.34 (d, 1H, J=4.8), 7.37 (s, 1H), 7.44 (s, 1H), 8.56 (d, 1H, J=4.8); 13C NMR (CDCl3) δ 45.7, 46.9, 55.5, 56.1, 56.6, 82.7, 98.5, 102.2, 106.7, 110.2, 120.2, 121.5, 122.9, 121.5, 122.9, 133.8, 145.9, 148.0, 148.3, 148.5, 149.0, 149.6, 151.0, 170.0; HRMS calcd for C23H24IN3O5H, 550.0839; found 550.0823.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-31bda3988c404fd48796201503635a77
Source dataset
uspto-grants-2010_08
Patent number
US07781587B2

Reaction notes

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