Phthalic Anhydride → 2-(3-fluoro-4-methylphenyl)-1H-isoindole-1,3(2H)-dione

HRID 1861937

반응식

HRID 1861937 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[C:10]1(=O)[O:15][C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C(N(CC)CC)C>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[C:13](=[O:14])[C:12]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]3[C:10]2=[O:15])[CH:6]=[CH:7][C:8]=1[CH3:9]

참가 물질

5

반응물 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 99573-Fluoro-4-methylaniline

생성물 1

HCID 6833332-(3-fluoro-4-methylphenyl)-1H-isoindole-1,3(2H)-dione수율 73.3%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A mixture of 3-fluoro-4-methylaniline (12.5 g), phthalic anhydride (17.8 g), triethylamine (27.9 ml) and chloroform (100 ml) was heated under reflux for 6 days and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed successively with 2 N HCl and a saturated aqueous sodium chloride solution; the organic layer was then dried with anhydrous sodium sulfate and concentrated under reduced pressure. Subsequently, chloroform was added to the resulting residue and the insoluble matter was filtered off whereas the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, chloroform methanol=98:2) to give 18.7 g of the titled compound (yield, 73%).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 6 days
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed successively with 2 N HCl
  6. dry with materialthe organic layer was then dried with anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionSubsequently, chloroform was added to the resulting residue
  9. filtrationthe insoluble matter was filtered off whereas the filtrate
  10. concentrationwas concentrated under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography (eluent, chloroform methanol=98:2)

출처 및 근거

ORD 기록
ord-cc0864c902174e3a862fafb9e2138856
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534546B1

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