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

HRID 1586147Notes

Reaction equation

HRID 1586147 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[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+]>C(O)(=O)C>[CH2:20]([N:19]1[C:15]([NH:14][C:2]2[C:3](=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:16][CH:17]=[N:18]1)[CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 172872-Chloro-5-nitrobenzoic acidHCID 3373101-Ethyl-1H-pyrazol-5-amine

Product 1

HCID 21217728N-(1-ethylpyrazol-5-yl)-5-nitroanthranilic acidYield 68.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-chloro-5-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)2H2O (0.5 g) is refluxed for 24 hours. The reaction mixture is cooled to room temperature, poured into ice waterl and acidified with acetic acid to a pH of 5. A solid forms which is collected by filtration and dried to afford 3.8 g (68%) of N-(1-ethylpyrazol-5-yl)-5-nitroanthranilic acid.

Workup

  1. temperatureis refluxed for 24 hours
  2. additionpoured into ice waterl
  3. filtrationA solid forms which is collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-c4049b1dc4be46148f888b845d119425
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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