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

HRID 1861937

反応式

HRID 1861937 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-cc0864c902174e3a862fafb9e2138856
出典データセット
uspto-grants-2003_03
特許番号
US06534546B1

関連ノート

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