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

HRID 1586149Notes

Reaction equation

HRID 1586149 reaction equation
Cl[C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:14][C:15]1[N:19]([CH2:20][CH3:21])[N:18]=[CH:17][CH:16]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:20]([N:19]1[C:15]([NH:14][C:2]2[C:3](=[CH:7][CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:16][CH:17]=[N:18]1)[CH3:21]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 74482-Chloro-4-nitrobenzoic acidHCID 11430Potassium CarbonateHCID 3373101-Ethyl-1H-pyrazol-5-amine

Product 1

HCID 21217705N-(1-ethylpyrazol-5-yl)-4-nitroanthranilic acidYield 63.3%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-chloro-4-nitrobenzoic acid (4.03 g, 0.02 mol), 5-amino-1-ethylpyrazole (2.22 g, 0.02 mol), DMF (25 ml), K2CO3 (2.76 g, 0.02 mol) and Cu(OAc)2. H2O (0.5 g) is refluxed for 24 hours. The reaction mixture is cooled to room temperature, poured into ice water and then acidified with acetic acid to a pH of 5. A solid forms which is collected by filtration and dried to afford 3.5 g (63%) of N-(1-ethylpyrazol-5-yl)-4-nitroanthranilic acid.

Workup

  1. filtrationA solid forms which is collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-1d6cc3cdea1e4719818b6de8e5662f08
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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