Dimethylformamide → N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid

HRID 613288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 613288
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:13][C:14]1[N:18]([CH2:19][CH3:20])[N:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:19]([N:18]1[C:14]([NH:13][C:2]2[C:3](=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:15][CH:16]=[N:17]1)[CH3:20]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 899062-Bromo-5-methoxybenzoic acidHCID 3373101-Ethyl-1H-pyrazol-5-amine

Produkt 1

HCID 19592240N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acidAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-5-methoxybenzoic acid (141.5 g, 0.61 mol), 5-amino-1-ethylpyrazole (68 g, 0.61 mol), K2CO3 (84.2 g, 0.61 mol), DMF (500 mL) and Cu(OAc)2 (3 g) was refluxed for about 2 days. The reaction mixture was cooled and then was poured into water (1500 mL). The mixture was acidified with acetic acid and the resulting solid was collected by filtration and dried to afford 110 g of N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid.

Aufarbeitung

  1. temperaturewas refluxed for about 2 days
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe resulting solid was collected by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4473a5e2474c4370bf2094bd0ade90b9
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008226

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