Hydrazine hydrate (1:1) → 3-amino-1H-indazole-5-carboxylic Acid

HRID 537139

Reaktionsgleichung

Reaktionsgleichung von HRID 537139
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1F)[C:6]([OH:8])=[O:7])#[N:2].O.[NH2:14][NH2:15]>C(O)C>[NH2:2][C:1]1[C:3]2[C:11](=[CH:10][CH:9]=[C:5]([C:6]([OH:8])=[O:7])[CH:4]=2)[NH:15][N:14]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 27739323-Cyano-4-fluorobenzoic acid

Produkt 1

HCID 115718843-amino-1H-indazole-5-carboxylic AcidAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 3-cyano-4-fluorobenzoic acid (980.0 mg, 5.94 mmol) in ethanol (6 mL), was added hydrazine hydrate (0.89 mL, 17.8 mmol). The reaction was heated at reflux for 3 hours. The reaction was cooled to room temperature and ethanol was removed under reduced pressure. The resultant yellow oil was taken up in water (50 mL) and basified with 1 N aqueous sodium hydroxide (5 mL). The solution was washed once with ethyl acetate (25 mL). The aqueous phase was acidified to pH=3 with 6 N aqueous hydrochloric acid and was allowed to stir at room temperature for 1 hour. The resulting precipitate was collected by filtration and dried under vacuum to give the title compound (612 mg, 48%) as a pink solid. +ESI (M+H) 178.1; 1H NMR (400 MHz, DMSO-d6, δ): 8.42-8.47 (m, 1H), 7.76 (dd, J=8.8, 1.6 Hz, 1H), 7.21 (d, J=8.8 Hz, 1H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 hours
  3. customethanol was removed under reduced pressure
  4. washThe solution was washed once with ethyl acetate (25 mL)
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e0b6aea40fa14edd8313bb2ccaa04762
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859773B2

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