Hydrochloric Acid → HCID 23356921, compound

HRID 233766Notes

Reaction equation

HRID 233766 reaction equation
C([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:11]=2)[CH:6]=1)(=O)C.Cl.[OH-].[Na+]>COCCO>[NH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:11]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23356926N-[6-(2-Pyridinylmethoxy)-2-naphthalenyl]acetamide

Product 1

HCID 23356921HCID 23356921, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

To a solution of 2-acetylamino-6-(2-pyridylmethyloxy)-naphthalene (0.76 g,) in 2-methoxyethanol (15 ml) was added 1N-hydrochloric acid (15 ml) and the resulting mixture was stirred with heating under reflux for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, made basic with an aqueous solution of sodium hydroxide, and then extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title compound (0.65 g) as the crude product. The NMR spectrum is as follows.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ba87386a06944cdacd378eaf93fef4c
Source dataset
uspto-grants-1997_01
Patent number
US05594016

Reaction notes

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