Hydroxylamine → HCID 58487787, compound

HRID 1406346Notes

Reaction equation

HRID 1406346 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:19]O>CN(C=O)C>[F:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:19]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86658816HCID 86658816, compound

Product 1

HCID 58487787HCID 58487787, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

180 mg (0.73 mmol) of 2-fluoro-4-(4-methoxy-phenoxy)-benzaldehyde were stirred with 180 μl (3 mmol) of hydroxylamine solution (50% in water) in 5 ml DMF at 100° C. for 1 h and then stirred overnight at ambient temperature. The mixture was evaporated down, dissolved in 10 ml of 7M methanolic ammonia and combined with 50 mg Raney nickel. It was then shaken for 4 h at ambient temperature and 3 bar hydrogen pressure. The catalyst was removed by suction filtering, the residue was evaporated down and purified by reversed-phase chromatography.

Workup

  1. customThe mixture was evaporated down
  2. dissolutiondissolved in 10 ml of 7M methanolic ammonia
  3. stirringIt was then shaken for 4 h at ambient temperature
  4. customThe catalyst was removed by suction
  5. filtrationfiltering
  6. customthe residue was evaporated down
  7. custompurified by reversed-phase chromatography

Sources & evidence

ORD record
ord-49ea95d380fc427dbacfe627fd0d6005
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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