Iodine → 3-Iodo-1-methoxynaphthalene

HRID 5294

반응식

HRID 5294 반응식
N[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.S(=O)(=O)(O)O.C1C2C(=CC=CC=2)C=CC=1.N([O-])=O.[Na+].[I-:33].[K+].II>O.C(Cl)Cl>[I:33][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

9

반응물 6

HCID 807IodineHCID 931NaphthaleneHCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 1510414-Methoxy-2-naphthylamineHCID 23668193Sodium Nitrite

생성물 1

HCID 186926573-Iodo-1-methoxynaphthalene수율 18.3%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

50 g of 3-amino-1-methoxynaphthalene was added to 750 mL of 6 N sulfuric acid. The mixture was heated to dissolve the naphthalene and the resulting solution was cooled to 0° C. To the resulting slurry of amine hydrosulfate salt at 0° C. was added a solution of 20 g of sodium nitrite in 30 mL of water. The resulting mixture stirred at 0° C. for 1 hour and was then poured into a solution of 100 g of potassium iodide and 20 g of iodine in 400 mL water. After stirring for 1 hour at room temperature, 250 mL methylene chloride was added. The layers were separated and the aqueous portion was extracted with 3×100 mL methylene chloride. The organic portion was combined with the methylene chloride extracts and was washed with 3×75 mL saturated sodium bisulfite, dried over anhydrous magnesium sulfate, filtered, and stripped. The resulting product was pre-adsorbed onto silica and eluted with hexane. The appropriate fractions were combined, concentrated and the residual oil was further purified by HPLC to yield 15 g of 3-iodo-1-methoxynaphthalene as a yellow oil. The structure was confirmed by NMR.

후처리

  1. temperatureThe mixture was heated
  2. stirringAfter stirring for 1 hour at room temperature
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with 3×100 mL methylene chloride
  5. washwas washed with 3×75 mL saturated sodium bisulfite
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. washeluted with hexane
  9. concentrationconcentrated
  10. customthe residual oil was further purified by HPLC

출처 및 근거

ORD 기록
ord-45091bce8d8d4124bcddaf8e105dd9d8
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244771

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