2-Iodobenzoic acid → N-(1,3-Dimethyl-5-pyrazolyl)anthranilic acid

HRID 597214

Reaktionsgleichung

Reaktionsgleichung von HRID 597214
C(=O)([O-])[O-].[K+].[K+].I[C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[NH2:17][C:18]1[N:22]([CH3:23])[N:21]=[C:20]([CH3:24])[CH:19]=1>[Cu].O>[CH3:23][N:22]1[C:18]([NH:17][C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10]([OH:12])=[O:11])=[CH:19][C:20]([CH3:24])=[N:21]1

Komponenten

6

Edukt 3

HCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

Produkt 1

HCID 615796N-(1,3-Dimethyl-5-pyrazolyl)anthranilic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of 4.84 grams of potassium carbonate in 18 ml. of water were added in succession 8.0 grams of o-iodobenzoic acid, 3.88 grams of 5-amino-1,3-dimethyl pyrazole and 0.8 gram of the copper catalyst. The mixture was stirred at reflux for 5 hours. There was then added an additional 50 milliliters of water, the mixture being refluxed an additional 30 minutes and then filtered through diatomaceous earth. The filtrate was digested with decolorizing carbon, heated to reflux and filtered. The filtrate was cooled and acidified with 3N aqueous hydrochloric acid to produce N-(1,3-dimethyl-5-pyrazolyl)anthanilic acid, mp 175°-189° C., recrystallized from ethanol to give needles, mp 204°-206° C.

Aufarbeitung

  1. temperatureat reflux for 5 hours
  2. temperaturethe mixture being refluxed an additional 30 minutes
  3. filtrationfiltered through diatomaceous earth
  4. temperatureheated
  5. temperatureto reflux
  6. filtrationfiltered
  7. temperatureThe filtrate was cooled

Quellen und Nachweise

ORD-Eintrag
ord-5d623112a673452e9b2f6d07eb485d5d
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04013665

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