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

HRID 375863Notes

Reaction equation

HRID 375863 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+]>CC([O-])=O.CC([O-])=O.[Cu+2].O.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

7

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 2

HCID 165397Cupric acetate monohydrateCatalystHCID 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)2.H2O (0.5 g) was refluxed for 24 hours. The reaction mixture was cooled to room temperature, poured into ice-water and acidified with acetic acid to a pH of 5. A solid formed which was collected by filtration and dried to afford 3.8 g (68%) of N-(1-ethylpyrazol-5-yl)-5-nitroanthranilic acid.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customA solid formed which
  3. filtrationwas collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-916249bbb8de48e48e8bfd4b9c6b7bfd
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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