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

HRID 375853Notes

Reaction equation

HRID 375853 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].CN(C=O)C.[NH2:18][C:19]1[N:23]([CH2:24][CH3:25])[N:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].O>[CH2:24]([N:23]1[C:19]([NH:18][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:20][CH:21]=[N:22]1)[CH3:25]

Participants

7

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 99.9%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-bromo-5-methoxybenzoic acid (39.3 g, 0.17 mol), DMF (150 ml), 5-amino-1-ethylpyrazole (18.5 g, 0.17 mol), potassium carbonate (23.5 g, 0.17 mol) and Cu(OAc)2 (0.6 g) was refluxed for about 2 days. The reaction mixture was cooled, poured into water and acidified to a pH of 5. A precipitate formed which was collected by filtration, washed with water and dried to afford 44.37 g (62%) of N-(1-ethylpyrazol-5-yl)-5-methoxyanthranilic acid.

Workup

  1. temperaturewas refluxed for about 2 days
  2. temperatureThe reaction mixture was cooled
  3. customA precipitate formed which
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-856650bf2d234727a7757d17d4b28906
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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