Dimethylformamide → N-(1-ethylpyrazol-5-yl)-5-bromoanthranilic acid

HRID 1586167Notes

Reaction equation

HRID 1586167 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C=O)C.[NH2:17][C:18]1[N:22]([CH2:23][CH3:24])[N:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:23]([N:22]1[C:18]([NH:17][C:2]2[C:3](=[CH:7][C:8]([Br:11])=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:19][CH:20]=[N:21]1)[CH3:24]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 118912,5-Dibromobenzoic acidHCID 3373101-Ethyl-1H-pyrazol-5-amine

Product 1

HCID 19592213N-(1-ethylpyrazol-5-yl)-5-bromoanthranilic acidYield 45.1%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2,5-dibromobenzoic acid (25 g, 0.09 mol), DMF (200 ml), 5-amino-1-ethylpyrazole (10 g, 0.09 mol), Cu(OAc)2 (1 g) and K2CO3 (12.3 g, 0.09 mol) is heated at reflux for about 2 days. The reaction mixture is poured into water, acidified with acetic acid, and the precipitate which forms is collected by filtration to afford 12.6 g of N-(1-ethylpyrazol-5-yl)-5-bromoanthranilic acid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for about 2 days
  3. filtrationthe precipitate which forms is collected by filtration

Sources & evidence

ORD record
ord-27eadd314c9c4136a748827486697d84
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

Loading…