Hydrochloric Acid → 4-Chloro-3-methyl-1H-pyrazole-5-carboxylic acid

HRID 528935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528935
[Cl:1][C:2]1[C:3]([C:8]([O:10]CC)=[O:9])=[N:4][NH:5][C:6]=1[CH3:7].[OH-].[Na+].Cl>CO.C1COCC1>[Cl:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][NH:5][C:6]=1[CH3:7]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 604759ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate2×

Produkt 1

HCID 176889814-Chloro-3-methyl-1H-pyrazole-5-carboxylic acidAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate (Intermediate 1A, 2.01 g, 10.7 mmol) in MeOH (8.2 mL) and THF (8.2 mL) was added 2N aq. NaOH solution (27 mL, 53.3 mmol). The reaction mixture was stirred at room temperature overnight, then cooled to 0° C. and neutralized with 1N aq. HCl solution (pH=3-4). The resulting solid was collected by filtration and washed with water to give the title compound (1.50 g, 87%) as a white solid. 1H NMR (DMSO-d6) δ 2.19 (br s, 3H); MS (ESI+) m/z 160.9 (M+H)+.

Aufarbeitung

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-1e0a740b74704675bb6831cfb7f6da09
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346795B2

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