Chlorosuccinimide → 2,3-Dichloro-N-methyl-4-pyridinecarboxamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([NH:7][CH3:8])=[O:6].[Li+].CC([N-]C(C)C)C.C1C(=O)N([Cl:27])C(=O)C1>C1COCC1>[Cl:1][C:2]1[C:3]([Cl:27])=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([NH:7][CH3:8])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
2-Chloro-N-methyl-isonicotinamide (12-2, 1.19 g, 6.98 mmol) was dissolved in 20 mL anhydrous THF and the solution was cooled to −78° C. LDA (2M, 7.33 mL, 14.7 mmol) was added dropwise and the reaction turns orange. After 15 min NCS (1.02 g, 7.67 mmol) was added and the reaction was allowed to warm to RT. After 1 h at RT HPLC shows ˜3:1 starting material/product. The reaction was quenched with water, extracted 3× w/ EtOAc, and the organic phases were dried over Na2SO4, filtered, and concentrated. The residue vias purified by preparative reverse phase HPLC to afford the pure titled compound. 1H NMR (CDCl3) δ8.36 (d, 1H, J=4.8 Hz), 7.41 (d, 1H, J=4.8 Hz), 6.10 (bs, 1H), 3.05 (d, 3H, J=4.9 Hz).
Workup
- temperatureto warm to RT
- customThe reaction was quenched with water
- extractionextracted 3× w/ EtOAc
- dry with materialthe organic phases were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue vias purified by preparative reverse phase HPLC
Sources & evidence
- ORD record
- ord-11c8dec04712449d81faee2ff76ba4ab
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06586423B2
Reaction notes
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