4-Aminophenol → Ethyl 7-(4-Hydroxyanilino)-1H-pyrazolo[4,3-b]pyridine-6-carboxylate

HRID 1731296

Reaktionsgleichung

Reaktionsgleichung von HRID 1731296
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[CH:13]=[N:14][NH:15][C:3]=12.[CH:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[C:18]([OH:23])[CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C(O)C>[OH:23][C:18]1[CH:19]=[CH:20][C:21]([NH:22][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]3[CH:13]=[N:14][NH:15][C:3]=23)=[CH:16][CH:17]=1

Komponenten

6

Edukt 3

HCID 4034-AminophenolHCID 10340Sodium CarbonateHCID 20038759Ethyl 7-chloro-1H-pyrazolo[4,3-B]pyridine-6-carboxylate

Produkt 1

HCID 135973927Ethyl 7-(4-Hydroxyanilino)-1H-pyrazolo[4,3-b]pyridine-6-carboxylateAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 7-chloro-1H pyrazolo[4,3-b]pyridine-6-carboxylate (1.0 g, 0.004 mole) and p-aminophenol (1.0 g, 0.009 mole) were stirred together in ethyl acetate (200 ml) under nitrogen for 48 hours, the temperature being maintained between -10° and -5° C. The ethyl acetate was removed under reduced pressure to give a yellow solid. This solid was dissolved in aqueous ethanol and the pH adjusted to pH8 with 10% sodium carbonate solution. The resulting solid was filtered off washed with water and dried. Recrystallization from methanol/ethyl acetate gave the title compound as a pale yellow solid (650 mg, 50%), m.p. 286°-287° C. (decomposition)

Aufarbeitung

  1. temperaturethe temperature being maintained between -10° and -5° C
  2. customThe ethyl acetate was removed under reduced pressure
  3. customto give a yellow solid
  4. filtrationThe resulting solid was filtered off
  5. washwashed with water
  6. customdried
  7. customRecrystallization from methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-bb145c7884934c8a9b9dac3e58acf3d0
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04621089

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