Anthranilic Acid → HCID 22124879, compound

HRID 1857937Notes

Reaction equation

HRID 1857937 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].Cl[C:12]1[CH:25]=[CH:24][C:15]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])=[CH:14][C:13]=1[N+:26]([O-:28])=[O:27].C(=O)([O-])[O-].[K+].[K+].C(O)CC(C)C>[Cu].CCOCC.O>[C:16]([C:15]1[CH:24]=[CH:25][C:12]([NH:4][C:3]2[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]([OH:10])=[O:9])=[C:13]([N+:26]([O-:28])=[O:27])[CH:14]=1)(=[O:17])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 227Anthranilic AcidHCID 11430Potassium CarbonateHCID 31260Isoamyl AlcoholHCID 417434-Chloro-3-nitrobenzophenone

Product 1

HCID 22124879HCID 22124879, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of anthranilic acid (1.37 g, 10 mmol.), 4-chloro-3-nitrobenzophenone (2.88 g, 11 mmol.), anhydrous potassium carbonate (powder, 2.77 g, 20 mmol.), copper (powder, 50 mg), and isoamyl alcohol (25 mL) was stirred and heated for one hour under reflux. The reaction mixture was cooled to room temperature, and stirred for 15 minutes after addition of water (30 mL) and ether (30 mL). The insoluble red-brown solid was collected by filtration and washed with water and ether. The red-brown solid mainly comprising a potassium salt of the desired compound was suspended in water (40 mL). To the suspension was added 2M hydrochloric acid until an aqueous portion of the suspension showed approximately pH 2. The suspension was vigorously stirred for one hour at room temperature. The deposited crystalline precipitate was collected by filtration and washed with several portions of water and ether. The washed precipitate was placed under reduced pressure at 60° C. for 3 hours to dryness. Thus, 2.34 g (65%) of the desired compound was obtained as a yellow-orange crystalline product.

Workup

  1. temperatureheated for one hour
  2. temperatureunder reflux
  3. stirringstirred for 15 minutes
  4. filtrationThe insoluble red-brown solid was collected by filtration
  5. washwashed with water and ether
  6. additionTo the suspension was added 2M hydrochloric acid until an aqueous portion of the suspension
  7. stirringThe suspension was vigorously stirred for one hour at room temperature
  8. filtrationThe deposited crystalline precipitate was collected by filtration
  9. washwashed with several portions of water and ether

Sources & evidence

ORD record
ord-a9c8a70ebbd345cfb2889351c450ac49
Source dataset
uspto-grants-2000_11
Patent number
US06150363

Reaction notes

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