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

HRID 375865

Reaction equation

HRID 375865 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].O.C(O)(=O)C>[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

7

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 2

HCID 165397Cupric acetate monohydrateCatalystHCID 176Acetic AcidSolvent

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) was refluxed for 24 hours. The reaction mixture was cooled to room temperature, poured into ice-water and then acidified with acetic acid to a pH of 5. A solid formed which was collected by filtration and dried to afford 3.5 g (63%) of N-(1-ethylpyrazol-5-yl)-4-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-ba8f3ffd56584595a660795c7f7173aa
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Linked notes

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