Hydrochloric Acid → 9-ethyl-9H-carbazole-3,6-dicarboxylic acid

HRID 745649

Reaktionsgleichung

Reaktionsgleichung von HRID 745649
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH2:20][CH3:21])[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([C:17](=[O:19])C)=[CH:11][CH:10]=3)(=[O:3])C.[OH-:22].[Na+].Cl[O-:25].[Na+].S(=O)(O)[O-].[Na+].Cl[O-].Cl>N1C=CC=CC=1>[CH2:20]([N:8]1[C:9]2[CH:10]=[CH:11][C:12]([C:17]([OH:22])=[O:19])=[CH:13][C:14]=2[C:15]2[C:7]1=[CH:6][CH:5]=[C:4]([C:1]([OH:25])=[O:3])[CH:16]=2)[CH3:21]

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61739HypochloriteHCID 6220833,6-Diacetyl-9-ethylcarbazoleHCID 23665760Sodium HypochloriteHCID 23665763Sodium Bisulfite

Produkt 1

HCID 37979149-ethyl-9H-carbazole-3,6-dicarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Nineteen grams of the 3,6-diacetyl-N-ethylcarbazole from Example 1 was dissolved in 800 ml pyridine and added to 400 ml of 5% aqueous sodium hydroxide in a 6-liter Erlenmeyer flask. While cooling the mixture in ice, 1429 ml of 5% sodium hypochlorite (bleach) was added. The reaction was allowed to stir 3.5 hours at room temperature. A concentrated solution of sodium bisulfite was added until no hypochlorite remained (starch-iodine test). The basic solution was neutralized with concentrated HCl and the precipitated diacid filtered. The yield of N-ethylcarbazole-3,6-dicarboxylic acid was 13.12 g.

Aufarbeitung

  1. temperatureWhile cooling the mixture in ice
  2. filtrationthe precipitated diacid filtered

Quellen und Nachweise

ORD-Eintrag
ord-f59fdcd24703440ca7f22b2cf0676c4c
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04599399

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