Citric Acid → 4-(5-Iodoindazole-1-yl)-benzoic acid

HRID 13138

Reaktionsgleichung

Reaktionsgleichung von HRID 13138
[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[NH2:2].C(=O)([O-])[O-].[Cs+].[Cs+].F[C:19]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:20]=1[CH:21]=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN1CCCC1=O>[I:27][C:24]1[CH:23]=[C:20]2[C:19](=[CH:26][CH:25]=1)[N:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1)[N:2]=[CH:21]2

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 120894-Hydrazinobenzoic acidHCID 162170582-Fluoro-5-iodobenzaldehyde

Produkt 1

HCID 593397454-(5-Iodoindazole-1-yl)-benzoic acidAusbeute 78,32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

4-Hydrazinobenzoic acid (11.32 g, 60 mmol) and cesiumcarbonate (58.65 g, 180 mmol) are added to 2-fluoro-5-iodobenzaldehyde (15 g, 60 mmol) in 300 mL N-methylpyrrolidon. After 1 h stirring at r.t., the reaction is heated for 4 h at 150° C. The reaction mixture is allowed to cool off and poured on 1 L ice water. The reaction mixture is acidified with citric acid and vigorously stirred at r.t. for 30 min. The precipitate is filtered off and given in ethyl acetate. The slurry is vigorously stirred for 1 h and sucked off. The filter residue (few material) is discarded and the filtrate evaporated. This residue which is contaminated with N-methylpyrrolidine is treated with 300 mL of a mixture of ethyl acetate/hexane (1:3) and stirred overnight. The precipitated crystals are sucked off and dried. 17.11 g (78.32%) of 4-(5-iodoindazole-1-yl)-benzoic acid are obtained.

Aufarbeitung

  1. temperaturethe reaction is heated for 4 h at 150° C
  2. temperatureto cool off
  3. stirringvigorously stirred at r.t. for 30 min
  4. filtrationThe precipitate is filtered off
  5. stirringThe slurry is vigorously stirred for 1 h
  6. customthe filtrate evaporated
  7. additionis treated with 300 mL of a mixture of ethyl acetate/hexane (1:3)
  8. stirringstirred overnight
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3020b7422e30417da0ba59e237a7512a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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