Phenylhydrazine → HCID 49839975, compound

HRID 68673

Reaction equation

HRID 68673 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[O:13])OC(=O)[NH:9][C:8]=2[CH:15]=1)([O-:3])=[O:2].[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[NH2:9][C:8]1[CH:15]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[C:12]([NH:23][NH:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 2820894-Nitro-isatoic anhydride

Product 1

HCID 49839975HCID 49839975, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 1000-mL 3-necked round-bottom flask, was placed a solution of 7-nitro-1H-benzo[d][1,3]oxazine-2,4-dione (56 g, 269.23 mmol, 1.00 equiv) in ethanol (500 mL), 1-phenylhydrazine (31.98 g, 296.11 mmol, 1.10 equiv). The resulting solution was heated to reflux for 5 min. The resulting mixture was then concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/petroleum ether (1:2˜1:0) and ethyl acetate/petroleum ether (1:1) to yield 2-amino-4-nitro-N′-phenylbenzohydrazide as a yellow solid. MS: 273 (MH+).

Workup

  1. customInto a 1000-mL 3-necked round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 5 min
  4. concentrationThe resulting mixture was then concentrated under vacuum

Sources & evidence

ORD record
ord-5f75d9a26c594fa3ba5a2d32857f915a
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Linked notes

Loading…