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

HRID 1456029

Reaktionsgleichung

Reaktionsgleichung von HRID 1456029
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:11][C:12]1[N:16]([CH3:17])[N:15]=[C:14]([CH3:18])[CH:13]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C>[CH3:17][N:16]1[C:12]([NH:11][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:13][C:14]([CH3:18])=[N:15]1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

Produkt 1

HCID 615796N-(1,3-Dimethyl-5-pyrazolyl)anthranilic acidAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2-iodobenzoic acid (14.9 g, 0.06 mol), 5-amino-1,3-dimethylpyrazole (6.7 g, 0.06 mol), DMF (125 ml), Cu(OAc)2 (0,4 g) and K2CO3 (8.28 g, 0.06 mol) was refluxed overnight. The reaction mixture was poured into ice-water (500 ml) and then was acidified with acetic acid to a pH of about 5. The solid which formed was collected by filtration, washed with water (100 ml) and dried. The solid was dissolved in hot CHCl3 (300 ml), filtered, dried over MgSO4 and evaporated to about 20 ml. Hexane (50 ml) was added and then the product was collected by filtration, washed with hexane (30 ml) and dried to afford 6.2 g of N-(1,3-dimethyl-pyrazol-5-yl)anthranilic acid, m.p. 210°-211° C.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. customThe solid which formed
  3. filtrationwas collected by filtration
  4. washwashed with water (100 ml)
  5. customdried
  6. dissolutionThe solid was dissolved in hot CHCl3 (300 ml)
  7. filtrationfiltered
  8. dry with materialdried over MgSO4
  9. customevaporated to about 20 ml
  10. additionHexane (50 ml) was added
  11. filtrationthe product was collected by filtration
  12. washwashed with hexane (30 ml)
  13. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1265f1e62e264ef3b62506da0c9ea6b6
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843956

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