Hydrochloric Acid → N-(2-chlorophenyl)pyridine-4-carboxamide
Reaction equation
NN[C:3](=[N:14][C:15]1[CH:20]=[CH:19][CH:18]=CC=1Cl)[C:4]1C=CC(S(C)(=O)=O)=CC=1.[O:22]=S(Cl)Cl.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH2:33].C(N(CC)CC)C.Cl>C(Cl)Cl.C(OCC)(=O)C>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:18](=[O:22])[C:19]1[CH:4]=[CH:3][N:14]=[CH:15][CH:20]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of isonicotinic acid 5 (1.0 g, 8.12 mmol) and SOCl2 (2.4 mL) in DCM (10 mL) was stirred for 2 hours and concentrated. The residue was dissolved in DCM (20 mL). To the solution was added 2-chlorobenzenamine (1.7 g, 8.15 mmol) and then triethylamine (1.4 mL, 10 mmol). The reaction mixture was stirred overnight at ambient temperature and ethyl acetate (50 mL) was added followed by 1N HCl (10 mL). The organic phase was washed with water and brine, dried and concentrated under reduced pressure to yield a light yellow solid. Yield: 1.5 g, 80%. N-(2-chlorophenyl)isonicotinamide 6 was used for the next step without further purification.
Workup
- concentrationconcentrated
- dissolutionThe residue was dissolved in DCM (20 mL)
- stirringThe reaction mixture was stirred overnight at ambient temperature
- washThe organic phase was washed with water and brine
- customdried
- concentrationconcentrated under reduced pressure
- customto yield a light yellow solid
- customN-(2-chlorophenyl)isonicotinamide 6 was used for the next step without further purification
Sources & evidence
- ORD record
- ord-40bf60b663c94054a8e2b8d7be2ce249
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096587B2
Reaction notes
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