Methanol → N-(2-amino-5-chloro-3-methylbenzoyl)-N'-methoxycarbonylhydrazine

HRID 2427035Notes

Reaction equation

HRID 2427035 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([CH3:14])[C:5]2[NH:6]C(=O)O[C:9](=[O:10])[C:4]=2[CH:3]=1.[C:15]([O:19][CH3:20])(=[O:18])[NH:16][NH2:17].CO>O>[NH2:6][C:5]1[C:12]([CH3:14])=[CH:13][C:2]([Cl:1])=[CH:3][C:4]=1[C:9]([NH:17][NH:16][C:15]([O:19][CH3:20])=[O:18])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 80519Methyl carbazateHCID 115502595-Chloro-3-methyl isatoic anhydride

Product 1

HCID 66854326N-(2-amino-5-chloro-3-methylbenzoyl)-N'-methoxycarbonylhydrazineYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.05 g of 6-chloro-8-methyl-1H-benzo[d]-1,3-oxazine-2,4-dione, 0.46 g of methyl carbazate and 20 ml of methanol was heated to reflux for 3 hours. After the reaction mixture was allowed to cool to around room temperature, water was poured thereto and the mixture was extracted with ethyl acetate three times. The resulting organic layer was concentrated under reduced pressure, and the residue was washed with toluene to obtain 0.77 g of N-(2-amino-5-chloro-3-methylbenzoyl)-N′-methoxycarbonylhydrazine of the formula:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. temperatureto cool to around room temperature
  4. extractionthe mixture was extracted with ethyl acetate three times
  5. concentrationThe resulting organic layer was concentrated under reduced pressure
  6. washthe residue was washed with toluene

Sources & evidence

ORD record
ord-67b0146654f24a0ebb57468fbf57e13e
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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