Anthranilic Acid → 3-Chloro-1-methylnaphthalene

HRID 1635947ノート

反応式

HRID 1635947 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=O)[CH:3]=1.O[C:11]1[CH:16]=[C:15](C)O[C:13](=O)[CH:12]=1.P(Cl)(Cl)(Cl)=O.FC(F)(F)C(O)=O.C(ON=O)CC(C)C.C(O)(=O)C1C(=CC=CC=1)N>COCCOC.CCCCCC.C(OC(=O)C)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:13]2[C:4]([CH:3]=1)=[CH:15][CH:16]=[CH:11][CH:12]=2

参加物

9

反応物 6

HCID 227Anthranilic Acid2 回HCID 6422Trifluoroacetic acidHCID 8053Isoamyl Nitrite2 回HCID 24813Phosphorus oxychlorideHCID 5391414-Chloro-6-methyl-2H-pyran-2-oneHCID 546757574-Hydroxy-6-methyl-2-pyrone

生成物 1

HCID 186736453-Chloro-1-methylnaphthalene収率 55%

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

実験手順

A three-neck round-bottomed flask was equipped with a reflux condenser and two addition funnels. Dry DME(200 ml) was introduced into the flask and 4-chloro-6-methyl-2-pyrone(3.24 g, 22.4 mmol) prepared according to the procedure described in a literature (see: M. J. D. Van Dam et F. KOGL, Recueil 83, 39, 1964) from 4-hydroxy-6-methyl-2-pyrone and phosphorusoxychloride, and trifluoroacetic acid(0.1 ml) were added thereto. Isoamylnitrite(3.15 g, 26.9 mmol) and anthranilic acid(3.69 g, 26.9 mmol) each dissolved in DME(50 ml) were introduced into the respective funnels. The isoamylnitrite solution and anthranilic acid solution were added dropwise simultaneously while keeping the reflux condition. After confirming that the starting materials were completely used, addition was stopped and the reaction solution was cooled. The solvent was removed under reduced pressure and the residue was dissolved in methyene chloride(100 ml) and the organic layer was sequentially washed with 5% aqueous hydrochloric acid solution, 5% aqueous sodium hydroxide solution and water. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to column chromatography(eluent: n-hexane/ethylacetate=9/1, v/v) to give 2.60 g(14.7 mmol, Yield 55%) of the title compound.

後処理

  1. customA three-neck round-bottomed flask was equipped with a reflux condenser
  2. additiontwo addition funnels
  3. customprepared
  4. additionwere added
  5. additionwere introduced into the respective funnels
  6. additionaddition
  7. temperaturethe reaction solution was cooled
  8. customThe solvent was removed under reduced pressure
  9. dissolutionthe residue was dissolved in methyene chloride(100 ml)
  10. washthe organic layer was sequentially washed with 5% aqueous hydrochloric acid solution, 5% aqueous sodium hydroxide solution and water
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-0d08edad138746408d90143f616efb8e
出典データセット
uspto-grants-2003_01
特許番号
US06511978B1

反応ノート

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