Aniline → 1,3-Dioxo-2-phenylisoindoline-5-carboxylic acid

HRID 858363

Reaktionsgleichung

Reaktionsgleichung von HRID 858363
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([OH:3])=[O:2].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)(=O)C>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([OH:3])=[O:2]

Komponenten

4

Edukt 2

HCID 6115AnilineHCID 11089Trimellitic anhydride

Produkt 1

HCID 207601,3-Dioxo-2-phenylisoindoline-5-carboxylic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

4-carboxyphthalic anhydride (benzene tricarboxylic acid anhydride) (1.0 g, 0.0052 mol), aniline (0.96 g, 0.0104 mol), and 70–80 mls of glacial acetic acid were added to a 100 ml round-bottom flask equipped with a reflux condenser, heating mantle and stir plate. The system was placed under a N2 atmosphere. A white solid precipitated out of the clear pale yellow solution within 1 minute. The mixture was heated to a gentle reflux. More precipitate formed during the course of the reaction. After 12 hours the mixture was cooled to room temperature and concentrated under vacuum with a rotary evaporator. The crude material was reprecipitated in 1,4-dioxane and IN HCl. The resultant white precipitate was filtered through a Buchner funnel and washed three times with 15 ml of water. The product was dried in air for 24 hours and then in vacuo for 48–72 hours to afford 1.25 g (90%) 109 as a white fluffy solid: mp=257–258° C.; Rf 0.83 (A): Rf 0.76 (B): Rf 0.62 (D): IR (cm−1): 2800–3125 (OH), 3071 (C═CH), 2665 (C—H), 1788 (C═O), 1719 (bs, C═O), 1602 (C═C), 1596 (C═C), 1504 (C═C), 1487 (C═C), 1399 (C—O), 1124 (C—O), 724 (C═CH); MS m/z (rel intensity) 267 (16), 266 (100).

Aufarbeitung

  1. customequipped with a reflux condenser
  2. temperatureheating mantle
  3. customA white solid precipitated out of the clear pale yellow solution within 1 minute
  4. temperatureThe mixture was heated to a gentle reflux
  5. customMore precipitate formed during the course of the reaction
  6. concentrationconcentrated under vacuum with a rotary evaporator
  7. customThe crude material was reprecipitated in 1,4-dioxane and IN HCl
  8. filtrationThe resultant white precipitate was filtered through a Buchner funnel
  9. washwashed three times with 15 ml of water
  10. customThe product was dried in air for 24 hours

Quellen und Nachweise

ORD-Eintrag
ord-6c6442b849d34b3c850d90b5e8e79bfc
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148352B2

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