1,2-Dimethoxyethane → N-(1-ethylpyrazol-5-yl)-4-carboxyanthranilic acid

HRID 1586159Notes

Reaction equation

HRID 1586159 reaction equation
Br[C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].COCCOC.[NH2:20][C:21]1[N:25]([CH2:26][CH3:27])[N:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:26]([N:25]1[C:21]([NH:20][C:2]2[C:3](=[CH:7][CH:8]=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:22][CH:23]=[N:24]1)[CH3:27]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 68513Bromoterephthalic acidHCID 3373101-Ethyl-1H-pyrazol-5-amine

Product 1

HCID 21217714N-(1-ethylpyrazol-5-yl)-4-carboxyanthranilic acidYield 45.4%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-bromoterephthalic acid (4.8 g, 0.02 mol), DME (50 ml), Cu(OAc)2 (0.2 g), 5-amino-1-ethylpyrazole (2.22 g, 0.02 mol) and K2CO3 (2.71 g, 0.02 mol) is heated at 135° C. overnight, then at reflux overnight. The reaction mixture is poured into water, acidified with acetic acid and the precipitate which forms is collected by filtration and dried to afford 2.5 g of N-(1-ethylpyrazol-5-yl)-4-carboxyanthranilic acid.

Workup

  1. temperatureat reflux overnight
  2. filtrationthe precipitate which forms is collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-5e04c109ec454e6786880bb6819313a5
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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