Water → 2-amino-N-ethylbenzamide

HRID 1864037Notes

Reaction equation

HRID 1864037 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

HCID 962WaterHCID 6341EthylamineHCID 8359Isatoic Anhydride

Product 1

HCID 17145582-amino-N-ethylbenzamideYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. concentrationthe reaction mixture was concentrated to 20 mL
  2. extractionextracted with EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe EtOAc layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3c4ca52da5f840c490d3c6f5ee27f03f
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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