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

HRID 1586149

Reaktionsgleichung

Reaktionsgleichung von HRID 1586149
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].C(O)(=O)C.O>[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

8

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 3

HCID 8895Cupric acetateKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

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) is refluxed for 24 hours. The reaction mixture is cooled to room temperature, poured into ice water and then acidified with acetic acid to a pH of 5. A solid forms which is collected by filtration and dried to afford 3.5 g (63%) of N-(1-ethylpyrazol-5-yl)-4-nitroanthranilic acid.

Aufarbeitung

  1. filtrationA solid forms which is collected by filtration
  2. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1d6cc3cdea1e4719818b6de8e5662f08
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05942520

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