2-Iodobenzoic acid → N-(1-cyclopentylpyrazol-5-yl) anthranilic acid

HRID 1586144

Reaktionsgleichung

Reaktionsgleichung von HRID 1586144
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]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:15]=[CH:14][CH:13]=1.COCCOC.C(=O)([O-])[O-].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C>[CH:17]1([N:16]2[C:12]([NH:11][C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]([OH:6])=[O:5])=[CH:13][CH:14]=[N:15]2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Komponenten

7

Edukt 4

HCID 69412-Iodobenzoic acidHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 10797921-cyclopentyl-1H-pyrazol-5-amine

Produkt 1

HCID 54038843N-(1-cyclopentylpyrazol-5-yl) anthranilic acidAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2-iodobenzoic acid (28 g, 0.113 mol), 5-amino-1-cyclopentylpyrazole (17 g, 0.113 mol), DME (100 ml), potassium carbonate (16 g, 0.113 mol) and Cu(OAc)2 (0.5 g) is refluxed overnight. The reaction mixture is poured into ice water, and acidified with acetic acid to a pH of 5. The gum which forms is extracted with CH2Cl2 and the CH2Cl2 layer is washed with water, dried over MgSO4, and evaporated to afford 21 g of N-(1-cyclopentyl pyrazol-5-yl) anthranilic acid.

Aufarbeitung

  1. temperatureis refluxed overnight
  2. extractionThe gum which forms is extracted with CH2Cl2
  3. washthe CH2Cl2 layer is washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5e2f2f46e0224fa4aface44e342bd7da
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05942520

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