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

HRID 375893

Reaction equation

HRID 375893 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) was refluxed overnight. The reaction mixture was cooled, poured into water and acidified with acetic acid. The resulting solid was collected by filtration and dried to afford 12.8 g (97%) of N-(1-ethylpyrazol-5-yl)-4,5-dimethoxyanthranilic acid.

Workup

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

Sources & evidence

ORD record
ord-01dd962ca2fc4c3ea128f9d346a5bb17
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Linked notes

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