Sodium Hydroxide → 1-Methyl-1H-indazole-7-carboxylic acid

HRID 1908110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1908110
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([O:13]C)=[O:12])[CH:4]=[N:3]1.[OH-].[Na+]>O1CCOCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=[O:12])[CH:4]=[N:3]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 37818682Methyl 1-methyl-1H-indazole-7-carboxylate

Produkt 1

HCID 569730131-Methyl-1H-indazole-7-carboxylic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Methyl 1-methylindazole-7-carboxylate (1 g, 5.3 mmol) was suspended in a mixture of sodium hydroxide (12 mL of 1.0 M, 12 mmol) and 1,4-dioxane (8.7 mL). The reaction mixture was heated at 80° C. for 30 minutes. The dioxane was evaporated off and the aqueous layer was extracted with ethyl acetate three times and the extracts were discarded. The aqueous layer was then acidified with 4M hydrochloric acid and then filtered and washed with 1M hydrochloric acid to yield 1-methylindazole-7-carboxylic acid (0.9 g, 97%) as a white solid. 1H NMR (400 MHz, DMSO) δ 13.31 (s, 1H), 8.20 (s, 1H), 8.01 (d, J=8.0 Hz, 1H), 7.87 (d, J=7.2 Hz, 1H), 7.21 (t, J=7.6 Hz, 1H), 4.18 (s, 3H).

Aufarbeitung

  1. customThe dioxane was evaporated off
  2. extractionthe aqueous layer was extracted with ethyl acetate three times
  3. filtrationfiltered
  4. washwashed with 1M hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-3521863a7c6641a99cadc6a101c696e0
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598164B2

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