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

HRID 977146Notes

Reaction equation

HRID 977146 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:13][C:14]1[N:18]([CH2:19][CH3:20])[N:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:19]([N:18]1[C:14]([NH:13][C:2]2[C:3](=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:15][CH:16]=[N:17]1)[CH3:20]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 899062-Bromo-5-methoxybenzoic acidHCID 3373101-Ethyl-1H-pyrazol-5-amine

Product 1

HCID 19592240N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acidYield 69%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-bromo-5-methoxybenzoic acid (141.5 g, 0.61 mol), 5-amino-1-ethylpyrazole (68 g, 0.61 mol), K2CO3 (84.2 g, 0.61 mol), DMF (500 mL) and Cu(OAc)2 (3 g) was refluxed for about 2 days. The reaction mixture was cooled and then was poured into water (1500 mL). The mixture was acidified with acetic acid and the resulting solid was collected by filtration and dried to afford 110 g of N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid.

Workup

  1. temperaturewas refluxed for about 2 days
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-3443edc2f5574a22a4981fc159c531be
Source dataset
uspto-grants-1997_03
Patent number
US05614530

Reaction notes

Loading…