Hydrochloric Acid → HCID 12132335, compound

HRID 851870Notes

Reaction equation

HRID 851870 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:6]([NH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:11]([C:12]([O:14]C)=[O:13])[C:10]=1[NH2:19])=O)#[N:2].[OH-].[Na+].Cl>C(O)(=O)C.CO>[C:1]([C:3]1[CH:4]=[C:5]([C:6]2[NH:8][C:9]3[CH:18]=[CH:17][CH:16]=[C:11]([C:12]([OH:14])=[O:13])[C:10]=3[N:19]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH:25]([CH3:27])[CH3:26])#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23023858HCID 23023858, compound

Product 1

HCID 12132335HCID 12132335, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of methyl 3-(3-cyano-4-isobutyloxybenzoylamino)anthranilate (341 mg, 0.93 mmol) in glacial acetic acid (10 mL) was heated under reflux for 2 hours, cooled, and placed under reduced pressure to distill the solvent off. To the residue was added a solution of sodium hydroxide (240 mg, 10 mmol) in methanol (20 mL), and the mixture was stirred for 5 hours at room temperature. The reaction mixture was made acidic by addition of aqueous 1M hydrochloric acid, and placed under reduced pressure to distill the solvent off. To the residue were added ethyl acetate and water. The organic portion was taken out, dried over anhydrous magnesium sulfate, and placed under reduced pressure to distill the solvent off. The residue was washed with hot toluene, to give 300 mg (yield 960) of the desired compound in the form of a pale yellow crystalline product.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperaturecooled
  3. distillationto distill the solvent off
  4. distillationto distill the solvent off
  5. additionTo the residue were added ethyl acetate and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationto distill the solvent off
  8. washThe residue was washed with hot toluene
  9. customto give

Sources & evidence

ORD record
ord-4ebe257bacd840edbeb9a32ed2682b23
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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