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

HRID 1458737Notes

Reaction equation

HRID 1458737 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) is dissolved in water (67 ml), and then 2-iodo-4-methoxybenzoic acid (25.3 g, 0.091 mol) is added, followed by 5-amino-1-ethylpyrazole (11.2 g, 0.101 mol) and finally copper (2.7 g). The reaction mixture is refluxed for 20 hours, cooled to room temperature. Then water (350 ml) is added, and the mixture is refluxed for 0.75 hours. The reaction mixture is cooled, and the product is 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 is refluxed for 20 hours
  2. temperaturethe mixture is refluxed for 0.75 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe product is collected by filtration
  5. customrecrystallized from ethanol
  6. customdried in an oven at 40° C.

Sources & evidence

ORD record
ord-f457b2d4ff7642a7874104c8572b7575
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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