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

HRID 1458754Notes

Reaction equation

HRID 1458754 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) is refluxed for about 2 days. The reaction mixture is cooled and then is poured into water (1500 ml). The mixture is acidified with acetic acid, and the resulting solid is collected by filtration and dried to afford 110 g of N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid.

Workup

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

Sources & evidence

ORD record
ord-01f07cae2b3a45a0bd831d35a3f92b11
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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