Dimethyl Sulfate → HCID 300058, compound

HRID 984706

Reaction equation

HRID 984706 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[CH:3]=1.S(OC)(O[CH3:17])(=O)=O.C(OCC)(=O)C.[OH-].[Na+]>O1CCOCC1>[Br:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][CH3:17])[CH:3]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 3484042-Amino-6-bromonaphthalene

Product 1

HCID 300058HCID 300058, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-6-bromonaphthalene (2.0 g) in 1,4-dioxane (30 ml) was added dropwise with dimethyl sulfate (1300 μl) and stirred at room temperature for 46 hours. The reaction mixture was added with ethyl acetate (90 ml) and then added with 1 N aqueous sodium hydroxide (5 ml). This mixture was extracted with ethyl acetate (150 ml×3). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=15:1) to obtain the title compound (Intermediate 27, 152 mg).

Workup

  1. extractionThis mixture was extracted with ethyl acetate (150 ml×3)
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography (hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-ab1d99d0d5f54fb4980e8525c0c08449
Source dataset
uspto-grants-2005_03
Patent number
US06867320B2

Linked notes

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