Hydrogen Peroxide → Ethyl 4-(aminocarbonyl)-3-(cyclopentylamino)benzoate

HRID 906144Notes

Reaction equation

HRID 906144 reaction equation
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[NH:14][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)#[N:2].C(=O)([O-])[O-:21].[K+].[K+].OO.O>CS(C)=O>[NH2:2][C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[NH:14][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:21]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 67404316Ethyl 4-cyano-3-(cyclopentylamino)benzoate

Product 1

HCID 67402438Ethyl 4-(aminocarbonyl)-3-(cyclopentylamino)benzoateYield 334.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of ethyl 4-cyano-3-(cyclopentylamino)benzoate (363 mg, 1.41 mmol), potassium carbonate (50 mg, 0.36 mmol), and 30% aqueous hydrogen peroxide (0.25 mL) in DMSO (1.5 mL) was stirred at 60° C. for 1 h. After cooling to room temperature, water was added and the resulting mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with water (10 mL) and brine (10 mL), dried over sodium sulfate, filtered and concentrated to give ethyl 4-(aminocarbonyl)-3-(cyclopentylamino)benzoate (333 mg, 86% yield). MS (EI) for C15H20N2O3: 277 (MH+).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with water (10 mL) and brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e7dfdf5d499a4003a770fd88f7018e26
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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