Acetovanillone → 2-methoxy-4-[(E)-C-methyl-N-[(4-nitrophenyl)methoxy]carbonimidoyl]phenol

HRID 41933

Reaction equation

HRID 41933 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][C:3]=1[O:11][CH3:12].Cl.[N+:14]([C:17]1[CH:25]=[CH:24][C:20]([CH2:21][O:22][NH2:23])=[CH:19][CH:18]=1)([O-:16])=[O:15]>>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][O:22]/[N:23]=[C:8](/[C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:11][CH3:12])[CH:4]=2)\[CH3:9])=[CH:24][CH:25]=1)([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 2214AcetovanilloneHCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)

Product 1

HCID 1359237252-methoxy-4-[(E)-C-methyl-N-[(4-nitrophenyl)methoxy]carbonimidoyl]phenolYield 55.3%

Procedure

4′-Hydroxy-3′-methoxyacetophenone (25) (150 mg, 0.903 mmol) was condensed with compound 19 (0.203 g, 0.992 mmol) according to the general procedure II-A defined above. After being heated for 3 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (20 mL), washed with H2O (2×15 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The residue thus obtained was subjected to flash chromatography (1:9 v/v ethyl acetate/hexane elution) to afford the title compound CP30261 (158 mg, 55%) as a yellow solid, m.p. 118.4-121.1° C., Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

Workup

  1. temperatureAfter being heated for 3 h the reaction mixture
  2. temperaturewas cooled
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe ensuing residue was dissolved in CH2Cl2 (20 mL)
  5. washwashed with H2O (2×15 mL)
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue thus obtained
  10. washwas subjected to flash chromatography (1:9 v/v ethyl acetate/hexane elution)

Sources & evidence

ORD record
ord-7eae7d2e5e7f4229acacea5a3aec6b6e
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Linked notes

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