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

HRID 375893

Reaktionsgleichung

Reaktionsgleichung von HRID 375893
[NH2:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[CH:4][CH:3]=1.Br[C:10]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:7]([N:6]1[C:2]([NH:1][C:10]2[C:11](=[CH:15][C:16]([O:21][CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=2)[C:12]([OH:14])=[O:13])=[CH:3][CH:4]=[N:5]1)[CH3:8]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2229632-Bromo-4,5-dimethoxybenzoic acidHCID 3373101-Ethyl-1H-pyrazol-5-amine

Produkt 1

HCID 21217688N-(1-ethylpyrazol-5-yl)-4,5-dimethoxyanthranilic acidAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-1-ethylpyrazole (5.0 g, 45 mmol), 2-bromo-4,5-dimethoxybenzoic acid (11.76 g, 45 mmol), K2CO3 (6.21 g, 45 mmol), Cu(OAc)2 (0.8 g, 400 mmol) and DMF (125 ml) was refluxed overnight. The reaction mixture was cooled, poured into water and acidified with acetic acid. The resulting solid was collected by filtration and dried to afford 12.8 g (97%) of N-(1-ethylpyrazol-5-yl)-4,5-dimethoxyanthranilic acid.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe resulting solid was collected by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-01dd962ca2fc4c3ea128f9d346a5bb17
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488055

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