Hydrazine hydrate (1:1) → HCID 22147957, compound

HRID 1823911Notes

Reaction equation

HRID 1823911 reaction equation
F[C:2]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.O.[NH2:21][NH2:22]>CCO>[N+:17]([C:14]1[CH:13]=[C:3]2[C:2](=[CH:16][CH:15]=1)[NH:22][N:21]=[C:4]2[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9859981N-Phenyl-2-fluoro-5-nitrobenzamide

Product 1

HCID 22147957HCID 22147957, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

2-Fluoro-5-nitro-N-phenyl benzamide (100 mg, 0.38 mmol) was suspended in EtOH (10 mL) and the mixture heated to 50° C. To the resulting solution was added hydrazine monohydrate (0.1 mL, 1.9 mmol). The mixture was heated at reflux for 30 minutes, at which time LC-MS showed complete conversion to the aryl hydrazine (ES+m/e=273). The mixture was allowed to cool to room temperature, concentrated and the residue partitioned between EtOAc and saturated ammonium chloride solution. The layers were separated and the organic phase was dried over sodium sulfate and concentrated to a yellow foam. The residue was dissolved in phosphorous oxychloride (5 mL) and the mixture heated at 90° C. for 30 minutes, then allowed to cool to room temperature and stirred overnight. The reaction mixture was concentrated and the residue partitioned between EtOAc and saturated sodium bicarbonate. The organic phase was dried over sodium sulfate and concentrated to afford the title compound as a red solid (80 mg, 83%); 1H NMR (400 MHz, DMSO) 6.88 (1H, t), 7.31 (2H, t), 7.51 (1H, d), 7.74 (2H, t), 8.17 (1H, dd), 9.24 (1H, s), 9.42 (1H, s), 12.74 (1H, s); MS (ES+) m/e=255.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 minutes, at which time LC-MS
  3. temperatureto cool to room temperature
  4. concentrationconcentrated
  5. customthe residue partitioned between EtOAc and saturated ammonium chloride solution
  6. customThe layers were separated
  7. dry with materialthe organic phase was dried over sodium sulfate
  8. concentrationconcentrated to a yellow foam
  9. dissolutionThe residue was dissolved in phosphorous oxychloride (5 mL)
  10. temperaturethe mixture heated at 90° C. for 30 minutes
  11. temperatureto cool to room temperature
  12. concentrationThe reaction mixture was concentrated
  13. customthe residue partitioned between EtOAc and saturated sodium bicarbonate
  14. dry with materialThe organic phase was dried over sodium sulfate
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-fad8b0e848c74a278393d6d4ef6aeed3
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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