Water → 6-chloro-N-(4-methoxyphenyl)nicotinamide

HRID 2276909Notes

Reaction equation

HRID 2276909 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[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.O>N1C=CC=CC=1>[Cl:1][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:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7732P-AnisidineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 14832696-chloro-N-(4-methoxyphenyl)nicotinamideYield 60.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

6-Chloronicotinoyl chloride (35, 17.6 g, 100.0 mmol) was added to p-anisidine (33, 12.3 g, 100.0 mmol) dissolved in pyridine (150 mL) solution and the resulting reaction mixture was heated for 3 hours at 120° C. After cooling to room temperature and adding water, the produced gray precipitate was filtered and washed with 5% sodium bicarbonate aqueous solution. Then, the solvent was removed under reduced pressure to obtain the target compound 6-chloro-N-(4-methoxyphenyl)nicotinamide (37, 16.0 g, 60%).

Workup

  1. customthe resulting reaction mixture
  2. temperatureAfter cooling to room temperature
  3. filtrationthe produced gray precipitate was filtered
  4. washwashed with 5% sodium bicarbonate aqueous solution
  5. customThen, the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-13e74a8e8a6c45c598dd839ee94399fe
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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