Hydrazine hydrate (1:1) → 1H-Indole-5-carbohydrazide

HRID 470914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470914
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12]C)=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O.[NH2:15][NH2:16]>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([NH:15][NH2:16])=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 2737635methyl 1H-indole-5-carboxylate

Produkt 1

HCID 227221541H-Indole-5-carbohydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A 100 mL round bottomed flask was charged with methyl 1H-indole-5-carboxylate (1.6 g, 9.13 mmol) and ethanol (20 mL). To this was added hydrazine monohydrate (10 g) and the mixture was placed under reflux for 7 days. The reaction mixture was concentrated to dryness and chloroform (80 mL) was added. The mixture was decanted and the insoluble white residue was washed once more with chloroform to remove traces of starting material. The white solid (1.54 g, 96%) was dried en vacuo and 1H NMR analysis was consistent with the solid compound. 1H NMR (DMSO d6, 400 MHz) δ 10.7 (br s, 1 H), 9.6 (br s, 2H), 8.21-8.15 (m, 1 H), 7.71 (dd, J=8.6 and 1.7 Hz, 1 H), 7.50 (d, J=8.6 Hz, 1 H), 7.44-7.39 ( m, 1 H) and 6.58-6.53 (m, 1 H).

Aufarbeitung

  1. temperatureunder reflux for 7 days
  2. concentrationThe reaction mixture was concentrated to dryness and chloroform (80 mL)
  3. additionwas added
  4. customThe mixture was decanted
  5. washthe insoluble white residue was washed once more with chloroform
  6. customto remove traces of starting material
  7. dry with materialThe white solid (1.54 g, 96%) was dried en vacuo and 1H NMR analysis

Quellen und Nachweise

ORD-Eintrag
ord-bc873179ecfd48df9dbf57d79ec4a980
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629167B2

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