Potassium Carbonate → N-(1-ethylpyrazol-5-yl)-4-methoxyanthranilic acid

HRID 977129Notes

Reaction equation

HRID 977129 reaction equation
C([O-])([O-])=O.[K+].[K+].I[C:8]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[NH2:19][C:20]1[N:24]([CH2:25][CH3:26])[N:23]=[CH:22][CH:21]=1>O.[Cu]>[CH2:25]([N:24]1[C:20]([NH:19][C:8]2[C:9](=[CH:13][CH:14]=[C:15]([O:17][CH3:18])[CH:16]=2)[C:10]([OH:12])=[O:11])=[CH:21][CH:22]=[N:23]1)[CH3:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3373101-Ethyl-1H-pyrazol-5-amineHCID 128221822-Iodo-4-methoxybenzoic acid

Product 1

HCID 19592233N-(1-ethylpyrazol-5-yl)-4-methoxyanthranilic acidYield 56.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent2×

Procedure

K2CO3 (13.94 g, 0.101 mol) was dissolved in water (67 ml) and then 2-iodo-4-methoxybenzoic acid (25.3 g, 0. 091 mol) was added, followed by 5-amino-1-ethylpyrazole (11.2 g, 0.101 mol) and finally copper (2.7 g). The reaction mixture was refluxed for 20 hours, cooled to room temperature and then water (350 ml) was added and the mixture was refluxed for 0.75 hours. The reaction mixture was cooled, and the product was collected by filtration, recrystallized from ethanol, and dried in an oven at 40° C. to afford 13.37 g (56%) of N-(1-ethylpyrazol-5-yl) -4-methoxyanthranilic acid, m.p. 130°-135° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 20 hours
  2. temperaturethe mixture was refluxed for 0.75 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe product was collected by filtration
  5. customrecrystallized from ethanol
  6. customdried in an oven at 40° C.

Sources & evidence

ORD record
ord-4d66e46e67274dd3b3349b4f8360ef76
Source dataset
uspto-grants-1997_03
Patent number
US05614530

Reaction notes

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