Ethanol → 2-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid

HRID 1037524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037524
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2C(C#N)=[C:15]3[C:10]([CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([CH:19]4[CH2:21][CH2:20]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.[OH-:25].[Na+].[CH2:27]([OH:29])[CH3:28]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:28]([C:27]([OH:25])=[O:29])=[C:15]3[C:10]([CH:11]=[C:12]([N+:22]([O-:24])=[O:23])[C:13]([CH:19]4[CH2:21][CH2:20]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 675140672-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carbonitrile

Produkt 1

HCID 677745202-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acidAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred suspension of compound (vi) (3.3 g, 8.6 mmol) in ethanol (35 mL) was added aqueous NaOH (3.44 g, 86 mmol) and the reaction mixture was heated to 90° C. and maintained for 15 h when TLC and LCMS showed the absence of SM and formation of product. Concentration of the solvent gave a crude residue which was dissolved in water and filtered. The filtrate was acidified with dilute HCl at which time the product precipitated and was filtered to give the crude product which was purified by acid-base treatment to give 2-(4-bromophenyl)-5-cyclopropyl-6-nitro-2H-indazole-3-carboxylic acid (vii) (2.2 g, 63%).

Aufarbeitung

  1. temperaturemaintained for 15 h when TLC and LCMS
  2. customConcentration of the solvent gave a crude residue which
  3. filtrationfiltered
  4. customprecipitated
  5. filtrationwas filtered
  6. customto give the crude product which
  7. customwas purified by acid-base treatment

Quellen und Nachweise

ORD-Eintrag
ord-8cba4bb1f3c0476b89a3b81eac0682fa
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546389B2

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