Hydrochloric Acid → Ethyl 4-amino-5-mesityl-1-methyl-1H-pyrazole-3-carboxylate

HRID 1154

Reaktionsgleichung

Reaktionsgleichung von HRID 1154
O=[C:2]([C:8](=[N:20]O)[C:9](=O)[C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl.[CH3:23][NH:24][NH2:25]>CO>[NH2:20][C:8]1[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:25][N:24]([CH3:23])[C:9]=1[C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6061MethylhydrazineHCID 178418386HCID 178418386, Verbindung

Produkt 1

HCID 15516666Ethyl 4-amino-5-mesityl-1-methyl-1H-pyrazole-3-carboxylateAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of the product of step B (4.0 g, 13.8 mmol) and 1.6 mL of 12N hydrochloric acid in 100 mL of methanol was added dropwise 0.63 g of methyl hydrazine at 0° C. The reaction mixture was stirred at room temperature 4 hours, and then concentrated. The resulting residue was partitioned between water and ethyl acetate. The organic phase was separated and washed once with brine. The ethyl acetate solution was then mixed with 100 mL of water. Solid Na2S2O4 in excess was added in small portion until TLC showed completion of the reduction. The organic phase was separated, washed with water and brine, and dried over Na2SO4. Evaporation gave 3.1 g of the title compound as a foam.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe resulting residue was partitioned between water and ethyl acetate
  3. customThe organic phase was separated
  4. washwashed once with brine
  5. additionThe ethyl acetate solution was then mixed with 100 mL of water
  6. additionSolid Na2S2O4 in excess was added in small portion until TLC
  7. customThe organic phase was separated
  8. washwashed with water and brine
  9. dry with materialdried over Na2SO4
  10. customEvaporation

Quellen und Nachweise

ORD-Eintrag
ord-75a3caa0644f40ee90d13cb00258ca5f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723608

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