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

HRID 375844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 375844
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) was 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 was refluxed overnight, cooled and then poured into ice-water. Acetic acid and HCl were added until a pH of about 4 was obtained. A precipitate formed which was 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 was refluxed overnight
  2. temperaturecooled
  3. customwas obtained
  4. customA precipitate formed which
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-13a1490ccfee48f5a6f304116bcedf54
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05488055

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