Water → 2-amino-N-ethylbenzamide
Reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.O.[CH2:14]([NH2:16])[CH3:15]>CO>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:16][CH2:14][CH3:15])=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A round-bottomed flask was charged with isatoic anhydride (5.0 g, 0.030 mol), 200 mL water, and 5 mL of methanol. Ethylamine (2N in methanol, 18.4 mL, 0.036 mol) was added slowly to the reaction mixture. After 1 h, the reaction mixture was concentrated to 20 mL. The reaction mixture was acidified with 1N HCl and extracted with EtOAc. The aqueous layer was basified with 6N NaOH and extracted with EtOAc. The EtOAc layer was dried over Na2SO4, filtered, and concentrated to dryness to afford 2-amino-N-ethylbenzamide (4.6 g, 91%): Mass (M+H)+=165.
Workup
- concentrationthe reaction mixture was concentrated to 20 mL
- extractionextracted with EtOAc
- extractionextracted with EtOAc
- dry with materialThe EtOAc layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-3c4ca52da5f840c490d3c6f5ee27f03f
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625903B2
Reaction notes
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