Isatoic Anhydride → HCID 178501125, compound

HRID 538030Notes

Reaction equation

HRID 538030 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][NH2:12])[CH2:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[K+].[K+].[C:19]12[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=1)[NH:24]C(=O)O[C:20]2=[O:21]>CC#N>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][NH:12][C:20](=[O:21])[C:19]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[NH2:24])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 8359Isatoic AnhydrideHCID 11430Potassium CarbonateHCID 178501118HCID 178501118, compound

Product 1

HCID 178501125HCID 178501125, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of trans-4-Aminomethyl-cyclohexanecarboxylic acid methyl ester (21.7 g, 127 mmol) in CH3CN (500 mL), K2CO3 (35 g, 254 mmol) and isatoic anhydride (20.7 g, 127 mmol) were added. The reaction was stirred at 70° C. overnight. The mixture was concentrated under reduced pressure and the residue was washed with 200 mL of H2O and the solid obtained was filtered. The titled compound (31.1 g, quantitative yield) was obtained as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washthe residue was washed with 200 mL of H2O
  3. customthe solid obtained
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-8aa3de1d8eda4ceeb56f08654b48cd92
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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