2-Chloro-3-pyridylamine → N-(2-chloro-pyridin-3-yl)-2,3-difluoro-benzamide

HRID 1715683Notes

Reaction equation

HRID 1715683 reaction equation
[NH2:1][C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[F:9][C:10]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13]>N1C=CC=CC=1>[Cl:8][C:3]1[C:2]([NH:1][C:12](=[O:13])[C:11]2[CH:15]=[CH:16][CH:17]=[C:18]([F:19])[C:10]=2[F:9])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 805282-Chloro-3-pyridylamineHCID 5195492,3-Difluorobenzoyl chloride

Product 1

HCID 55099857N-(2-chloro-pyridin-3-yl)-2,3-difluoro-benzamideYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.31 g 3-amino-2-chloropyridine (25.8 mmol) and 20 mL pyridine were mixed in an ice bath. 5.0 g 2,3-difluoro-benzoyl chloride (28.4 mmol) was then added. After return to room temperature and reaction for 4 hr, the reaction was quenched by water. After extraction three times by ethyl acetate, an ethyl acetate layer was collected and washed by 1M HCl solution. After drying, filtration, concentration, and purification by silicon-gel column, 6.4 g solid was obtained, with a yield of 93%.

Workup

  1. customAfter return to room temperature and reaction for 4 hr
  2. customthe reaction was quenched by water
  3. extractionAfter extraction three times by ethyl acetate
  4. customan ethyl acetate layer was collected
  5. washwashed by 1M HCl solution
  6. customAfter drying
  7. filtrationfiltration, concentration, and purification by silicon-gel column

Sources & evidence

ORD record
ord-15eade2f5a814988985aa876913a5626
Source dataset
uspto-grants-2010_09
Patent number
US07799918B2

Reaction notes

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