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

HRID 889323Notes

Reaction equation

HRID 889323 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

5

Reactant 4

HCID 10340Sodium CarbonateHCID 211563-MethoxybenzylamineHCID 24386Thionyl ChlorideHCID 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).

Workup

  1. customthe excess thionyl chloride evaporated under vacuum
  2. dissolutionThe residue was dissolved in DCM (2 ml)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-64fda189e703411e9f5984f58b34b7dc
Source dataset
uspto-grants-2012_08
Patent number
US08252818B2

Reaction notes

Loading…