Hydrochloric Acid → N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide

HRID 1862226Notes

Reaction equation

HRID 1862226 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]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 21933527N-[4-amino-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyl oxy}phenyl]acetamide

Product 1

HCID 21933517N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2.01 g of isoamyl nitrite in 1 ml of acetonitrile was added to a mixture of 2.0 g of N-[4-amino-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyl oxy}phenyl]acetamide, 1.13 g of copper(I) chloride, 2.31 g of copper(II) chloride and 20 ml of acetonitrile dropwise at room temperature, and the mixture was stirred for 1 hour. This reaction solution was poured into 2% hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 1.04 g of N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]acetamide.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d5e2f1d05f3b4a32b549a9372ee6db5d
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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