Water → N-(2,6-dichloro-pyridin-3-yl)-4-methoxy-benzamide

HRID 40716Notes

Reaction equation

HRID 40716 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[Cl:12][C:13]1[C:18]([NH2:19])=[CH:17][CH:16]=[C:15]([Cl:20])[N:14]=1.O>N1C=CC=CC=1>[Cl:12][C:13]1[C:18]([NH:19][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:17][CH:16]=[C:15]([Cl:20])[N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7477p-Anisoyl chlorideHCID 1128462,6-Dichloro-3-pyridylamine

Product 1

HCID 58220150N-(2,6-dichloro-pyridin-3-yl)-4-methoxy-benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

4-Methoxy-benzoyl chloride (4.15 mL, 30.7 mmol) was added dropwise to a stirred, cooled 0° C. mixture of 2,6-dichloro-pyridin-3-ylamine (5 g, 30.7 mmol) in pyridine (31 mL). Following addition, the reaction mixture was allowed to warm to room temperature and stirring was continued for 30 minutes, at which point the reaction mixture was poured into water causing the formation of a precipitate which was collected by filtration. The collected solids were washed with additional water before drying overnight in vacuo affording N-(2,6-dichloro-pyridin-3-yl)-4-methoxy-benzamide (8.66 g, 29.1 mmol, 95% yield) which was used in subsequent reactions without further purification. ES MS (M+H+)=297.

Workup

  1. additionaddition
  2. temperatureto warm to room temperature
  3. filtrationwas collected by filtration
  4. washThe collected solids were washed with additional water
  5. custombefore drying overnight in vacuo

Sources & evidence

ORD record
ord-401742739efe4f8dbe8bad0c9f5cf879
Source dataset
uspto-grants-2013_09
Patent number
US08530483B2

Reaction notes

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