Hydrazine hydrate (1:1) → HCID 57755841, compound

HRID 227727Notes

Reaction equation

HRID 227727 reaction equation
F[C:2]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)=O.O.[NH2:22][NH2:23]>CCO>[F:13][C:9]1[CH:8]=[C:7]([NH:6][C:4]2[C:3]3[C:2](=[CH:17][CH:16]=[C:15]([N+:18]([O-:20])=[O:19])[CH:14]=3)[NH:23][N:22]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 433774282-Fluoro-N-(3-fluoro-phenyl)-5-nitro-benzamide

Product 1

HCID 57755841HCID 57755841, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2-Fluoro-N-(3-fluoro-phenyl)-5-nitro-benzamide (1.1 μg, 4 mmol) was suspended in EtOH (25 mL) and the mixture heated to ˜60° C. To the resulting solution was added hydrazine monohydrate (1.06 mL, 20 mmol). The mixture was heated at reflux for 5 minutes and a yellow solid was precipitated out. The mixture was allowed to cool to room temperature then the solid was filtered off. The solid was dissolved in phosphorous oxychloride (40 mL) and the mixture heated at 90° C. for 1.5 hr then allowed to cool to room temperature and stirred for overnight. The reaction mixture was concentrated and partitioned between EtOAc and saturated sodium bicarbonate. The organic phase was dried over MgSO4 and concentrated to afford the title compound as a red solid (0.7 g, 64%). MS (ESI) m/z=273 [M+H]+. 1H NMR (400 MHz, d6-DMSO) δ 12.84 (s, 1H), 9.69 (s, 1H), 9.22 (d, J=2.0 Hz, 1H), 8.19 (dd, J=9.2 and 2.0 Hz, 1H), 7.77 (m, 1H), 7.54 (d, J=9.2 Hz, 1H), 7.37 (m, 2H), 6.69 (m, 1H)

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 minutes
  3. customa yellow solid was precipitated out
  4. temperatureto cool to room temperature
  5. filtrationthe solid was filtered off
  6. dissolutionThe solid was dissolved in phosphorous oxychloride (40 mL)
  7. temperaturethe mixture heated at 90° C. for 1.5 hr
  8. temperatureto cool to room temperature
  9. concentrationThe reaction mixture was concentrated
  10. custompartitioned between EtOAc and saturated sodium bicarbonate
  11. dry with materialThe organic phase was dried over MgSO4
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-b737c827c04a45bc918f5bec54db0ac7
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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