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

HRID 2108949Notes

Reaction equation

HRID 2108949 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-ee0d0f44c8284204a75f3aa17f9287b5
Source dataset
uspto-grants-2009_04
Patent number
US07514456B2

Reaction notes

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