Water → 2-[[3-Methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid

HRID 497939

Reaktionsgleichung

Reaktionsgleichung von HRID 497939
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:3]=1.I[C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(O)(=O)C>[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=[O:18])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:3]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 7351323-Methyl-1-(pyridin-2-yl)-1H-pyrazol-5-amine

Produkt 1

HCID 223201402-[[3-Methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (5.23 g, 30 mmol), o-iodobenzoic acid (8.93 g, 36 mmol), copper acetate (II) (0.654 g, 3.6 mmol), and potassium carbonate (4.98 g, 36 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 1 hour under an argon atmosphere. After the solution was cooled to room temperature, the mixture was added to water. The solution was made weakly acidic by the addition of acetic acid, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (8.64 g, 98% yield).

Aufarbeitung

  1. temperatureunder reflux for 1 hour under an argon atmosphere
  2. filtrationthe resulting crude crystals were collected by filtration
  3. washThe crystals were washed with water and air
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-233acd72c0c449d7a0646a20355f0b60
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949648B2

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