Dimethylformamide → N-(1-ethylpyrazol-5-yl)-4-nitroanthranilic acid

HRID 375865

Reaktionsgleichung

Reaktionsgleichung von HRID 375865
Cl[C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:14][C:15]1[N:19]([CH2:20][CH3:21])[N:18]=[CH:17][CH:16]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].O.C(O)(=O)C>[CH2:20]([N:19]1[C:15]([NH:14][C:2]2[C:3](=[CH:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:16][CH:17]=[N:18]1)[CH3:21]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 74482-Chloro-4-nitrobenzoic acidHCID 11430Potassium CarbonateHCID 3373101-Ethyl-1H-pyrazol-5-amine

Produkt 1

HCID 21217705N-(1-ethylpyrazol-5-yl)-4-nitroanthranilic acidAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 165397Cupric acetate monohydrateKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-4-nitrobenzoic acid (4.03 g, 0.02 mol), 5-amino-1-ethylpyrazole (2.22 g, 0.02 mol), DMF (25 ml), K2CO3 (2.76 g, 0.02 mol) and Cu(OAc)2.H2O (0.5 g) was refluxed for 24 hours. The reaction mixture was cooled to room temperature, poured into ice-water and then acidified with acetic acid to a pH of 5. A solid formed which was collected by filtration and dried to afford 3.5 g (63%) of N-(1-ethylpyrazol-5-yl)-4-nitroanthranilic acid.

Aufarbeitung

  1. temperaturewas refluxed for 24 hours
  2. customA solid formed which
  3. filtrationwas collected by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ba8f3ffd56584595a660795c7f7173aa
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488055

Verknüpfte Notizen

Wird geladen…