Dimethyl Sulfate → 6-Bromo-2-methoxy-N-methyl-1-naphthamide

HRID 480452Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([NH:14][CH3:15])=[O:13])=[C:7]([OH:16])[CH:6]=[CH:5]2.[CH3:17]OS(OC)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([NH:14][CH3:15])=[O:13])=[C:7]([O:16][CH3:17])[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 6-Bromo-2-hydroxy-N-methyl-1-naphthamide (1.20 g), dimethylsulfate (0.49 mL), and powdered K2CO3 (1.18 g) in anhydrous DMF (10 mL) was heated at 60° C. for 30 min. After dilution with 1N HCl, the resulting mixture was extracted with Ethyl acetate. The combined organic layers were washed with water and brine followed by drying over MgSO4. After removal of the solvent in vacuo, the residue was washed with hexane-AcOEt (1:1) to give the title compound (1.21 g) as a colorless powder.

Workup

extractionAfter dilution with 1N HCl, the resulting mixture was extracted with Ethyl acetate
washThe combined organic layers were washed with water and brine
dry with materialby drying over MgSO4
customAfter removal of the solvent in vacuo
washthe residue was washed with hexane-AcOEt (1:1)

Sources & evidence

ORD record: ord-a28776cc27d64c1197245c418599af5c
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649643B1

Reaction notes

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