Hydrochloric Acid → N-[6-(2-Pyridinylmethoxy)-2-naphthalenyl]acetamide

HRID 233765Notes

Reaction equation

HRID 233765 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](C(=NO)C)[CH:15]=2)[CH:10]=1.C1(C)C=CC(S(Cl)(=O)=[O:30])=CC=1.Cl.C(Cl)(Cl)Cl.CO.[N:41]1C=CC=[CH:43][CH:42]=1>>[C:42]([NH:41][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:10]=2)[CH:15]=1)(=[O:30])[CH3:43]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 21584188Chloroform methanolHCID 86179831HCID 86179831, compound

Product 1

HCID 23356926N-[6-(2-Pyridinylmethoxy)-2-naphthalenyl]acetamideYield 62%

Procedure

To a solution of 2-(2-pyridylmethyloxy)-6-(1-hydroxyiminoethyl)-naphthalene (1.23 g) in pyridine (15 ml) was added p-toluenesulfonyl chloride (1.45 g) and the resultant-mixture was stirred at room temperature for 24 hours. The reaction mixture was made acid with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium hydroxide and a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a residue. The residue was subjected to column chromatography on silica gel eluting with CHCl3 /MeOH to obtain the title compound (0.76 g, yield=62%). The NMR spectrum is as follows.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous solution of sodium hydroxide
  3. dry with materiala saturated saline solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue

Sources & evidence

ORD record
ord-46f8f545600445558f9fa3d714b3209b
Source dataset
uspto-grants-1997_01
Patent number
US05594016

Reaction notes

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