2,4-Dimethoxyaniline → 3-Pyridinecarboxamide, 6-chloro-N-(2,4-dimethoxyphenyl)-
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:14]=1[NH2:15]>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:15][C:14]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:13]=2[O:12][CH3:11])=[O:7])=[CH:9][CH:10]=1Participants
3
Procedure
The title compound was prepared from 6-chloronicotinoyl chloride and 2,4-dimethoxyaniline as described in Example 1. The reaction mixture was filtered to remove the precipitate and the filtrate was evaporated. The resulting solid was purified by CH2Cl2/hexane recrystallization to give a light purple solid in a yield of 59%. 1H NMR (DMSO-d6): 9.77 (s, 1H), 8.93 (s, 1H), 8.35-8.31 (m, 1H), 7.68 (d, J=7.8, 1H), 7.46 (d, J=9.0, 1H), 6.67 (d, J=2.4, 1H), 6.57-6.53 (m, 1H), 3.80 (s, 3H), 3.78 (s, 3H).
Workup
- filtrationThe reaction mixture was filtered
- customto remove the precipitate