2-Iodobenzoic acid → N-(1,3-Dimethyl-5-pyrazolyl)anthranilic acid

HRID 597214

Reaction equation

HRID 597214 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[NH2:17][C:18]1[N:22]([CH3:23])[N:21]=[C:20]([CH3:24])[CH:19]=1>[Cu].O>[CH3:23][N:22]1[C:18]([NH:17][C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10]([OH:12])=[O:11])=[CH:19][C:20]([CH3:24])=[N:21]1

Participants

6

Reactant 3

HCID 69412-Iodobenzoic acidHCID 11430Potassium CarbonateHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine

Product 1

HCID 615796N-(1,3-Dimethyl-5-pyrazolyl)anthranilic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent2×

Procedure

To a solution of 4.84 grams of potassium carbonate in 18 ml. of water were added in succession 8.0 grams of o-iodobenzoic acid, 3.88 grams of 5-amino-1,3-dimethyl pyrazole and 0.8 gram of the copper catalyst. The mixture was stirred at reflux for 5 hours. There was then added an additional 50 milliliters of water, the mixture being refluxed an additional 30 minutes and then filtered through diatomaceous earth. The filtrate was digested with decolorizing carbon, heated to reflux and filtered. The filtrate was cooled and acidified with 3N aqueous hydrochloric acid to produce N-(1,3-dimethyl-5-pyrazolyl)anthanilic acid, mp 175°-189° C., recrystallized from ethanol to give needles, mp 204°-206° C.

Workup

  1. temperatureat reflux for 5 hours
  2. temperaturethe mixture being refluxed an additional 30 minutes
  3. filtrationfiltered through diatomaceous earth
  4. temperatureheated
  5. temperatureto reflux
  6. filtrationfiltered
  7. temperatureThe filtrate was cooled

Sources & evidence

ORD record
ord-5d623112a673452e9b2f6d07eb485d5d
Source dataset
uspto-grants-1977_03
Patent number
US04013665

Linked notes

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