Dimethyl Sulfate → N-(7-methoxynaphthalen-1-yl)acetamide

HRID 863505Notes

Reaction equation

HRID 863505 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[CH:13]=[C:12]([OH:15])[CH:11]=[CH:10]2)(=[O:3])[CH3:2].S(OC)(O[CH3:20])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[CH:13]=[C:12]([O:15][CH3:20])[CH:11]=[CH:10]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 809461-Acetamido-7-naphthol

Product 1

HCID 11447230N-(7-methoxynaphthalen-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8-Acetamido-2-naphthol (21 g, 0.104 mol), dimethyl sulfate (15.1 g, 0.12 mol) and potassium carbonate (41 g, 0.3 mol) in acetone (200 mL) was stirred at room temperature for 48 h. Solids were removed by filtration and washed with methanol, and the filtrate evaporated. The residue was washed in 1:1 hexane:toluene, collected by filtration and dried (24.7 g).

Workup

  1. customSolids were removed by filtration
  2. washwashed with methanol
  3. customthe filtrate evaporated
  4. washThe residue was washed in 1:1 hexane
  5. filtrationtoluene, collected by filtration
  6. customdried (24.7 g)

Sources & evidence

ORD record
ord-6af2e0d4890a4fea8e82f0200997e77e
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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