N-2-Naphthalenylacetamide → HCID 13663774, compound

HRID 1270748Notes

Reaction equation

HRID 1270748 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)(=[O:3])[CH3:2].[F:15][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>CCOC(C)=O>[F:15][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][C:5]=1[NH:4][C:1](=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11394N-2-NaphthalenylacetamideHCID 2724933Selectfluor

Product 1

HCID 13663774HCID 13663774, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.95 g (10 mmol) of 2-acetylaminonaphthalene, and 7.1 g (20 mmol) of 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor®) in 30 mL of CH2CN is heated to reflux under an atmosphere of nitrogen for 24 hours. After cooling to room temperature, 50 mL of EtOAc is added and the mixture is washed with H2O and dried over MgSO4. Evaporation of the solvents gives a syrup that is purified by flash chromatography on silica gel (25% EtOAc/hexane) to give 1-fluoro-2-acetylaminonaphthalene.

Workup

  1. temperatureis heated
  2. temperatureto reflux under an atmosphere of nitrogen for 24 hours
  3. washthe mixture is washed with H2O
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvents
  6. customgives a syrup that
  7. customis purified by flash chromatography on silica gel (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-419799cfae6d4c5691385fcab24fa48d
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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