Potassium Hydroxide → 1H-Pyrazole-4-carboxylic acid, 5-(aminocarbonyl)-1-(4-methylphenyl)-

HRID 978943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 978943
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:6]=[CH:5][C:4]=1[C:15]([O:17]CC)=[O:16])#[N:2].[OH-:20].[K+]>O>[C:15]([C:4]1[CH:5]=[N:6][N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:1]([NH2:2])=[O:20])([OH:17])=[O:16]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 13772970Ethyl 5-cyano-1-(4-methylphenyl)-1H-pyrazole-4-carboxylate

Produkt 1

HCID 1637161H-Pyrazole-4-carboxylic acid, 5-(aminocarbonyl)-1-(4-methylphenyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To 10 g. of ethyl 5-cyano-1-(4-methylphenyl)-4 pyrazolecarboxylate was added 5.6 g. of potassium hydroxide and 200 ml. of water followed by enough water to cause solution. The mixture was stirred under reflux for 8 hours and allowed to stand for 3 days. It was then poured over ice, made acid and filtered. The solids from the filtration were heated in 100 ml. of ethyl acetate, and the undissolved solid was separated, dried and identified as 4.25 g. of the desired product, m.p. 260° dec. The product was identified by nuclear magnetic resonance analysis in DMSOd6. δ2.36 (s,3), methyl; 7.32 (d,2), aromatic; 7.45 (d,2), aromatic; 8.01 (s,1), pyrazole; 7.91 (s,1), carboxamide; 8.33 (s,1), carboxamide.

Aufarbeitung

  1. temperatureunder reflux for 8 hours
  2. additionIt was then poured over ice
  3. filtrationfiltered
  4. filtrationThe solids from the filtration
  5. temperaturewere heated in 100 ml
  6. customof ethyl acetate, and the undissolved solid was separated
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8a990cbdf3194e9ea98c568aadf9439d
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04666504

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