Sodium Carbonate → 6-chloro-N-(3-methoxybenzyl)nicotinamide

Reaction equation

Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][NH2:17].C(=O)([O-])[O-].[Na+].[Na+].S(Cl)([Cl:29])=O>>[Cl:29][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([O:12][CH3:11])[CH:14]=2)=[O:8])=[CH:4][N:3]=1

Participants

Reactant 4

HCID 10340Sodium Carbonate

HCID 211563-Methoxybenzylamine

HCID 24386Thionyl Chloride

HCID 2389326-Bromonicotinic acid

Product 1

HCID 94957946-chloro-N-(3-methoxybenzyl)nicotinamide

Procedure

6-Bromonicotinic acid (200 mg, 0.99 mmol) was heated at reflux in thionyl chloride (2 ml) for 3 hrs. The reaction was allowed to cool to room temperature and the excess thionyl chloride evaporated under vacuum. The residue was dissolved in DCM (2 ml), 3-methoxybenzylamine (137 mg, 0.10 mmol) and sodium carbonate (500 mg) were added to the solution. The reaction was stirred at room temperature for 4 hrs, filtered and the filtrate reduced to dryness under vacuum to give 6-chloro-N-(3-methoxybenzyl)nicotinamide. NMR: δH [2H6]-DMSO 9.29,(1H, t), 8.88,(1H, d), 8.28,(1H, dd), 7.66,(1H, d), 7.25,(1H, t), 6.90,(2H, m), 6.83,(1H, m), 4.47,(2H, d), 3.74,(3H, s).