Hydrochloric Acid → Anthranilamide

HRID 324514Notes

Reaction equation

HRID 324514 reaction equation
Cl.[N+:2]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8])([O-])=O.C(=O)([O-])[O-].[Na+].[Na+]>CO.[Fe]>[NH2:2][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 118762-Nitrobenzamide

Product 1

HCID 6942Anthranilamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Concentrated hydrochloric acid (140μL) was added to a solution of the nitrobenzamide, V.3 (147 mg, 0.30 mmol) in methanol (2 ml). Iron (72 mg) was added and the reaction mixture was heated to 80° C. for 2 hours, before cooling. The reaction mixture was basified (saturated sodium carbonate solution), extracted into ethyl acetate, dried over magnesium sulphate and the solvent removed in vacuo to yield an off-white solid which was purified using flash chromatography(ethyl acetate) to yield the desired 2-aminobenzamide, VI.3 (47 mg, 34%).

Workup

  1. temperaturebefore cooling
  2. extractionextracted into ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed in vacuo
  5. customto yield an off-white solid which
  6. customwas purified

Sources & evidence

ORD record
ord-26babed926144b1b90eb38edd92a4e13
Source dataset
uspto-grants-2001_04
Patent number
US06218393B1

Reaction notes

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