Dimethyl Sulfate → 6-bromo-N-methylnaphthalen-2-amine

HRID 984706

反応式

HRID 984706 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 3000586-bromo-N-methylnaphthalen-2-amine

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ab1d99d0d5f54fb4980e8525c0c08449
出典データセット
uspto-grants-2005_03
特許番号
US06867320B2

関連ノート

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