Aniline → Phthalanilic acid

HRID 1973033

Reaktionsgleichung

Reaktionsgleichung von HRID 1973033
[C@@H:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C@@H:2]1[CH2:3][CH:4]=[CH:5][CH2:6]2.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>COCCOC>[C:13]1([NH:12][C:10](=[O:11])[C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:7]([OH:9])=[O:8])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

4

Edukt 2

HCID 6115AnilineHCID 98495Tetrahydrophthalic anhydride, cis-

Produkt 1

HCID 78458Phthalanilic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Cis-4-cyclohexene-1,2-dicarboxylic anhydride (7.6 g., 0.05 mole) was dissolved in 150 ml. 1,2-dimethoxyethane and 4.7 g. aniline (0.05 mole) was added. The reaction mixture was heated to reflux for one hour and allowed to stand overnight. The solvent was evaporated. The product then obtained was purified by pouring into 200 ml. of 10% hydrochloric acid solution. This was extracted with diethyl ether, dried over anhydrous magnesium sulfate, filtered and the solvent stripped off. There was obtained 7.3 g. of the title compound. The structure was confirmed by infrared analysis and n.m.r.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for one hour
  3. customThe solvent was evaporated
  4. customThe product then obtained
  5. customwas purified
  6. additionby pouring into 200 ml
  7. extractionThis was extracted with diethyl ether
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThere was obtained 7.3 g

Quellen und Nachweise

ORD-Eintrag
ord-7299cca8886c48749aa90c2713a02290
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03996043

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