Dimethylformamide → N-(1-ethylpyrazol-5-yl)-4,5-dimethoxyanthranilic acid

HRID 1586177Notes

Reaction equation

HRID 1586177 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[CH:4][CH:3]=1.Br[C:10]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:7]([N:6]1[C:2]([NH:1][C:10]2[C:11](=[CH:15][C:16]([O:21][CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=2)[C:12]([OH:14])=[O:13])=[CH:3][CH:4]=[N:5]1)[CH3:8]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2229632-Bromo-4,5-dimethoxybenzoic acidHCID 3373101-Ethyl-1H-pyrazol-5-amine

Product 1

HCID 21217688N-(1-ethylpyrazol-5-yl)-4,5-dimethoxyanthranilic acidYield 97.6%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 5-amino-1-ethylpyrazole (5.0 g, 45 mmol), 2-bromo-4,5-dimethoxybenzoic acid (11.76 g, 45 mmol), K2CO3 (6.21 g, 45 mmol), Cu(OAc)2 (0.8 g, 400 mmol) and DMF (125 ml) is refluxed overnight. The reaction mixture is cooled, poured into water and acidified with acetic acid. The resulting solid is collected by filtration and dried to afford 12.8 g (97%) of N-(1-ethylpyrazol-5-yl)-4,5-dimethoxyanthranilic acid.

Workup

  1. temperatureis refluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe resulting solid is collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-f5df32e6af6d40d596175af554282810
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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