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

HRID 2108950Notes

Reaction equation

HRID 2108950 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-53a9302137334316b2bb95031038d1a4
Source dataset
uspto-grants-2009_04
Patent number
US07514456B2

Reaction notes

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