Hydrochloric Acid → N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide
Reaction equation
N(OCCC(C)C)=O.N[C:10]1[C:15]([O:16][C:17]2[C:18]([O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][C:13]([NH:29][C:30](=[O:32])[CH3:31])=[C:12]([F:33])[CH:11]=1.[ClH:34]>C(#N)C.[Cu]Cl.[Cu](Cl)Cl>[Cl:34][C:10]1[C:15]([O:16][C:17]2[C:18]([O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][C:13]([NH:29][C:30](=[O:32])[CH3:31])=[C:12]([F:33])[CH:11]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 2.01 g of isoamyl nitrite in 1 ml of acetonitrile was added dropwise to a mixture of 2.0 g of N-[4-amino-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide, 1.13 g of copper(I) chloride, 2.31 g of copper(II) chloride, and 20 ml of acetonitrile at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was poured into 2% hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 1.04 g of N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-38ae94464f75441baf093f82c03508c6
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115544B2
Reaction notes
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