1-(3-Hydroxy-4-methoxyphenyl)ethanone → 5-[(E)-N-[(4-fluorophenyl)methoxy]-C-methylcarbonimidoyl]-2-methoxyphenol

HRID 41937

Reaction equation

HRID 41937 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10](=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[F:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][O:20][NH2:21])=[CH:17][CH:16]=1>>[F:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][O:20]/[N:21]=[C:10](/[C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([OH:1])[CH:3]=2)\[CH3:11])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 956931-(3-Hydroxy-4-methoxyphenyl)ethanoneHCID 12800721o-(4-Fluorobenzyl)hydroxylamine hydrochloride

Product 1

HCID 251002525-[(E)-N-[(4-fluorophenyl)methoxy]-C-methylcarbonimidoyl]-2-methoxyphenolYield 80.4%

Procedure

Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(4-fluorobenzyl)hydroxylamine hydrochloride (29) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 24 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL) and the resulting solution washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution) to afford the title compound CP30266 (70 mg, 80%) as a pale-purple waxy-oil, Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

Workup

  1. temperatureAfter being heated for 24 h the reaction mixture
  2. temperaturewas cooled
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe ensuing residue was dissolved in CH2Cl2 (15 mL)
  5. washthe resulting solution washed with H2O (2×10 mL)
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe oil thus obtained
  10. washwas subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution)

Sources & evidence

ORD record
ord-33a86ec32c7f452895ed1319b948ae9d
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Linked notes

Loading…