Anthranilic Acid → Bentranil

HRID 2386945Notes

Reaction equation

HRID 2386945 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11](Cl)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)(=O)C(Cl)=O.C(=O)([O-])O.[Na+]>N1C=CC=CC=1.CN(C)C=O>[C:12]1([C:11]2[O:9][C:1](=[O:10])[C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=3[N:4]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 7412Benzoyl chlorideHCID 65578Oxalyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 13926Bentranil

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Anthranilic acid (1.0 g, 7.29 mmol) was dissolved in pyridine (10 mL), benzoyl chloride (1.13 g, 8.02 mmol) was slowly added on an ice bath, and stirred at 50° C. overnight. The solvent was distilled off under reduced pressure, the residue was dissolved in dry methylene chloride (20 mL), oxalyl chloride (925 mg, 7.29 mmol) and a catalytic amount of dimethylformamide were added on an ice bath, and stirred at room temperature for 4 hours. Saturated sodium hydrogen carbonate aqueous solution was added, the mixture was extracted with methylene chloride, and the organic phase was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the residue was washed by diethyl ether/heptane, and the target substance (1.13 g, 69%) was obtained as a light yellow solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in dry methylene chloride (20 mL)
  3. stirringstirred at room temperature for 4 hours
  4. extractionthe mixture was extracted with methylene chloride
  5. dry with materialthe organic phase was dried with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. washthe residue was washed by diethyl ether/heptane
  8. customthe target substance (1.13 g, 69%) was obtained as a light yellow solid

Sources & evidence

ORD record
ord-4fdf7ff2c6b2412e8485ef3b2cb7093f
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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