Hydrazine → bemoradan

HRID 1588334Notes

Reaction equation

HRID 1588334 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([C:12](=O)[CH:13]([CH3:18])[CH2:14][C:15](O)=[O:16])=[CH:11][C:5]=2[O:4][CH2:3]1.[NH2:20][NH2:21]>C(O)C>[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]3[CH:13]([CH3:18])[CH2:14][C:15](=[O:16])[NH:20][N:21]=3)=[CH:11][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 11065271HCID 11065271, compound

Product 1

HCID 5362399bemoradanYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(3,4-Dihydro-3-oxo-1,4(2H)-benzoxazin-7-yl)-4-oxo-3-methylbutyric acid (31 g, 0.12 moles) was dissolved in ethanol (300 ml) and anhydrous hydrazine (4.7 ml, 0.15 moles) was added. The mixture was heated at reflux overnight. White crystals formed after the mixture was cooled. The crystals were collected by filtration and washed well with ethanol. The solid was dried under vacuum giving 28.5 g (93%) of the titled compound, mp 299°-302° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customWhite crystals formed after the mixture
  4. temperaturewas cooled
  5. filtrationThe crystals were collected by filtration
  6. washwashed well with ethanol
  7. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-9ab5686fe7e246cc8b97ed1e68459d7b
Source dataset
uspto-grants-1993_06
Patent number
US05221742

Reaction notes

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