Methyl iodide → N-(7-methoxynaphthalen-1-yl)acetamide

HRID 895219

Reaction equation

HRID 895219 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[NH:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH3:16][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[NH:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 809461-Acetamido-7-naphthol

Product 1

HCID 11447230N-(7-methoxynaphthalen-1-yl)acetamideYield 86.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of N-(7-hydroxynaphthyl)acetamide (175.4 g, 0.872 mol), potassium carbonate (301 g, 2.18 mol), and acetone (1 l) was added iodomethane (270 mL, 4.36 mol). The reaction mixture was refluxed for 6 hr, cooled to room temperature, and the solvent removed. The residue was filtered through silica with ethyl acetate and triturated with ethyl acetate to yield 161.6 g (86%) of a gray solid. An analytical sample was further purified by preparative reverse phase HPLC to yield the title compound as a white solid: mp 154-155° C.; 1H NMR (DMSO-d6): δ 2.19 (3H, s), 3.90 (3H, s), 7.19 (1H, dd, J=2.39 Hz, J=8.94 Hz), 7.29-7.34 (2H, m), 7.39 (1H; d, J=1.86 Hz), 7.75-7.68 (2H, m), 7.87 (1H, d, J=8.96 Hz), 9.82 (1H, s); MS (ESI) m/z 216 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hr
  2. customthe solvent removed
  3. filtrationThe residue was filtered through silica with ethyl acetate
  4. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-2b833808d63b4480b219f28475730c38
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Linked notes

Loading…