Phthalic Anhydride → Benzoic acid, 2-[(1-butyl-2-methyl-1H-indol-3-yl)carbonyl]-

HRID 1388574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1388574
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH2:12]([N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]1[CH3:25])[CH2:13][CH2:14][CH3:15].[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[CH2:12]([N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[C:1]([OH:6])=[O:11])=[O:5])=[C:17]1[CH3:25])[CH2:13][CH2:14][CH3:15]

Komponenten

5

Edukt 3

HCID 6811Phthalic AnhydrideHCID 30848831H-Indole, 1-butyl-2-methyl-HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 105559Benzoic acid, 2-[(1-butyl-2-methyl-1H-indol-3-yl)carbonyl]-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a stirred mixture containing 7.4 g. of phthalic anhydride and 16.0 g. of 1-butyl-2-methylindole at 0°-5° C. was added portionwise 13.3 g. of aluminum chloride. The mixture was diluted with 50 ml. of benzene and stirred overnight at room temperture. The reaction mixture was poured into 200 ml. of 5% hydrochloric acid and the product extracted with benzene. The benzene extracts were shaken with dilute aqueous potassium hydroxide. The aqueous alkaline layer was separated, cooled with ice and brought to pH 4 with acetic acid. The precipitated product was collected and dried to give 2-(1-butyl-2-methyl-3-indolylcarbonyl)benzoic acid, m.p. 88°-92° C.

Aufarbeitung

  1. additionTo a stirred mixture containing 7.4 g
  2. additionThe mixture was diluted with 50 ml
  3. additionThe reaction mixture was poured into 200 ml
  4. extractionof 5% hydrochloric acid and the product extracted with benzene
  5. customThe aqueous alkaline layer was separated
  6. temperaturecooled with ice
  7. customThe precipitated product was collected
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-311ef40cd0ed4a3eb60242b56be9c126
Quelldatensatz
uspto-grants-1984_02
Patentnummer
US04431819

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