Thionyl Chloride → 1H-indole-3-carbohydrazide

HRID 1697443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1697443
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.S(Cl)(Cl)=O.O.[NH2:18][NH2:19]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([NH:18][NH2:19])=[O:12])=[CH:2]1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 24654Hydrazine hydrate (1:1)HCID 69867Indole-3-Carboxylic Acid

Produkt 1

HCID 271991H-indole-3-carbohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Indole-3-carboxylic acid (500 mg, 3.1 mmol) was stirred at room temperature with thionyl chloride (5 mL, 68 mmol) for 20 hours. The solution was concentrated under vacuum and the residue was taken up in ether (10 mL) and concentrated to dryness (repeated three times) to ensure removal of the thionyl chloride. The resulting solid was dissolved in ether (5 mL) and added to an ice cooled solution of hydrazine hydrate (600 mg, 12 mmol) in tetrahydrofuran (5 mL). After 30 minutes, the solid was collected by filtration, washed with 5% NaOH and water, and dried under vacuum at 50° C. The crude hydrazide was recrystallized from 95% ethanol to provide the title compound. 1H NMR (300 MHz, CD3OD) δ 7.11-7.22 (m, 2 H), 7.42 (dd, J=7, 2 Hz, 1 H), 7.83 (s, 1 H), 8.02-8.08 ppm (m, 1 H); MS (DCI/NH3) m/z 176 (M+H)+.

Aufarbeitung

  1. concentrationThe solution was concentrated under vacuum
  2. concentrationconcentrated to dryness (repeated three times)
  3. customremoval of the thionyl chloride
  4. dissolutionThe resulting solid was dissolved in ether (5 mL)
  5. filtrationthe solid was collected by filtration
  6. washwashed with 5% NaOH and water
  7. customdried under vacuum at 50° C
  8. customThe crude hydrazide was recrystallized from 95% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-41c6a027f4aa45b89a94eb2eb72bfc1b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163915B2

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