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

HRID 375875

Reaktionsgleichung

Reaktionsgleichung von HRID 375875
Br[C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C=O)C.[NH2:19][C:20]1[N:24]([CH2:25][CH3:26])[N:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:25]([N:24]1[C:20]([NH:19][C:2]2[C:3](=[CH:7][CH:8]=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:21][CH:22]=[N:23]1)[CH3:26]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 68513Bromoterephthalic acidHCID 3373101-Ethyl-1H-pyrazol-5-amine

Produkt 1

HCID 21217714N-(1-ethylpyrazol-5-yl)-4-carboxyanthranilic acidAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A mixture of 2-bromoterephthalic acid (4.8 g, 0.02 mol), DMF (50 ml), Cu(OAc)2 (0.2 g), 5-amino-1-ethylpyrazole (2.22 g, 0.02 mol) and K2CO3 (2.71 g, 0.02 mol) was heated at 135° C. overnight, then at reflux overnight. The reaction mixture was poured into water, acidified with acetic acid and the precipitate which formed was collected by filtration and dried to afford 2.5 g of N-(1-ethylpyrazol-5-yl)-4-carboxyanthranilic acid.

Aufarbeitung

  1. temperatureat reflux overnight
  2. customthe precipitate which formed
  3. filtrationwas collected by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9cc4debf8de34b8cb8ec94ed6aa9f752
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488055

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