4-(n-Hexadecanamido)-3-methylbenzoic acid → 2-(n-Pentadecyl)indole-5-carboxylic acid

HRID 2412621

Reaktionsgleichung

Reaktionsgleichung von HRID 2412621
[C:1]([NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=1[CH3:28])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CC(C)([O-])C.[K+]>CCN(C1C=CC=CC=1)CC>[CH2:2]([C:1]1[NH:18][C:19]2[C:20]([CH:28]=1)=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

4

Edukt 2

HCID 128000094-(n-Hexadecanamido)-3-methylbenzoic acidHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 127972172-(n-Pentadecyl)indole-5-carboxylic acidAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7061N,N-DiethylanilineLösungsmittel

Versuchsvorschrift

A stirred mixture of 4-(n-hexadecanamido)-3-methylbenzoic acid (4 g), potassium tert-butoxide (4 g) and diethylaniline (10 ml) was refluxed for 3.5 hours. The fraction boiling at less than 200° C. during the reaction was collected. The reaction mixture was left to cool to room temperature and was then acidified with 10% w/v hydrochloric acid. The solid was filtered off, dried and recrystallized from toluene to give 2-(n-pentadecyl)indole-5-carboxylic acid (2.7 g), m.p. 108°-110° C.

Aufarbeitung

  1. temperaturewas refluxed for 3.5 hours
  2. customThe fraction boiling at less than 200° C. during the reaction was collected
  3. waitThe reaction mixture was left
  4. filtrationThe solid was filtered off
  5. customdried
  6. customrecrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-8e24d62e57b14d2bb9612e013455e462
Quelldatensatz
uspto-grants-1985_01
Patentnummer
US04493843

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