Methyl iodide → HCID 58064854, compound

HRID 400709Notes

Reaction equation

HRID 400709 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:15])[C:3]=1O.[C:17]([O-:20])([O-])=O.[K+].[K+].[CH3:23]I>CN(C=O)C.O>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([O:15][CH3:23])[C:3]=1[O:20][CH3:17]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58064933HCID 58064933, compound

Product 1

HCID 58064854HCID 58064854, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 75 mg of 1-bromo-2,3-dihydroxy-5-nitronaphthalene in 3.0 ml of DMF was added K2CO3 and Methyl iodide. The resulting solution was heated at 50° C. overnight after which the reaction mixture was diluted with water and extracted with ethyl acetate. Column chromatography using 30% ethyl acetate in hexane afforded the product, 1-bromo-5-nitro-2,3-dimethoxynaphthalene as a yellow solid. (Yield: 60 mg; 1H NMR (CDCl3) δ 3.99 (s, 3H), 4.04 (s, 3H), 7.45-7.53 (m, 1H), 7.98 (s, 1H), 8.21 (dd, J=6.0 Hz, 1.2 Hz, 1H), 8.51 (dd, J=6.0 Hz, 1.2 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-8726aba6bb944008b3eaa796feae745a
Source dataset
uspto-grants-2014_06
Patent number
US08741917B2

Reaction notes

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