P-Anisidine → 6-chloro-N-(4-methoxyphenyl)nicotinamide

HRID 2037237Notes

Reaction equation

HRID 2037237 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:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].S(Cl)([Cl:28])=O>>[Cl:28][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[O:8])=[CH:4][N:3]=1

Participants

5

Reactant 4

HCID 7732P-AnisidineHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 2389326-Bromonicotinic acid

Product 1

HCID 14832696-chloro-N-(4-methoxyphenyl)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), p-anisidine (123 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-(4-methoxyphenyl)nicotinamide. NMR: δH [2H6]-DMSO 10.37, (1H, b), 8.94, (1H, d), 8.34, (1H, dd), 7.70, (1H, d), 7.66, (2H, m), 6.95, (2H, m), 3.75, (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-552b3630e8494a9881c4f4c2e8ee3ec9
Source dataset
uspto-grants-2013_11
Patent number
US08575204B2

Reaction notes

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