Hydrochloric Acid → 2-((1-Ethyl-1H-pyrazol-5-yl)amino)benzoic acid

HRID 1586128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586128
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[NH2:17][C:18]1[N:22]([CH2:23][CH3:24])[N:21]=[CH:20][CH:19]=1.Cl>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Cu+2].O.C(O)(=O)C>[CH2:23]([N:22]1[C:18]([NH:17][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:19][CH:20]=[N:21]1)[CH3:24]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 3373101-Ethyl-1H-pyrazol-5-amine

Produkt 1

HCID 154274682-((1-Ethyl-1H-pyrazol-5-yl)amino)benzoic acidAusbeute 42,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 165397Cupric acetate monohydrateKatalysatorHCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-iodobenzoic acid (54 g, 0.218 mol) in DMF (570 ml) is added potassium carbonate (33.4 g, 0.242 mol), followed by 5-amino-1-ethylpyrazole (24.2 g, 0.218 mol) and finally Cu(OAc)2.H2O (0.9 g, 0.0045 mol). The reaction mixture is refluxed overnight, cooled and then poured into ice water. Acetic acid and HCl are added until a pH of about 4 is obtained. A precipitate forms which is collected by filtration, washed with water and dried to afford 21.4 g of N-(1-ethylpyrazol-5-yl) anthranilic acid.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed overnight
  2. temperaturecooled
  3. customis obtained
  4. filtrationA precipitate forms which is collected by filtration
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-22aac3f4894442f5ba4a2651c4f6fb45
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05942520

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