Ethanol → Ethyl 2-(2-aminobenzoyl)hydrazine-1-carboxylate

HRID 2427031Notes

Reaction equation

HRID 2427031 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.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[NH:14][NH2:15].C(O)C>C(OCC)(=O)C>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:15][NH:14][C:13]([O:17][CH2:18][CH3:19])=[O:16])=[O:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 8359Isatoic AnhydrideHCID 20064Hydrazinecarboxylic acid, ethyl ester

Product 1

HCID 13693259Ethyl 2-(2-aminobenzoyl)hydrazine-1-carboxylateYield 66.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 16.3 g of isatoic anhydride, 10.4 g of ethyl carbazate and 50 ml of ethanol was heated to reflux for 3 hours. After the reaction mixture was allowed to cool to around room temperature, ethyl acetate was added thereto and the mixture was washed with water two times. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was washed with methyl tert-butyl ether to obtain 14.9 g of N-(2-aminobenzoyl)-N′-ethoxycarbonylhydrazine of the formula:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureto cool to around room temperature
  4. washthe mixture was washed with water two times
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe resulting residue was washed with methyl tert-butyl ether

Sources & evidence

ORD record
ord-428a5f9f09c34157a1c7e36aafdca6ac
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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