Pyridine → 2-methoxy-5-[(E)-C-methyl-N-[(4-nitrophenyl)methoxy]carbonimidoyl]phenol

HRID 41926

Reaction equation

HRID 41926 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.[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].N1C=CC=CC=1>CCO>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][O:22]/[N:23]=[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:24][CH:25]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)HCID 956931-(3-Hydroxy-4-methoxyphenyl)ethanone

Product 1

HCID 885675852-methoxy-5-[(E)-C-methyl-N-[(4-nitrophenyl)methoxy]carbonimidoyl]phenolYield 89.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ketone 12 (200 mg, 1.20 mmol) in EtOH (2.0 mL) was treated with compound 19 (0.27 g, 1.32 mmol) and pyridine (0.5 mL) and the resulting mixture heated at reflux for 3 h then cooled and the solvent evaporated under reduced pressure. The ensuing residue was partitioned between CH2Cl2 (10 mL) and H2O (10 mL). The separated aqueous fraction was extracted with CH2Cl2 (1×5.0 ml) and the combined organic fractions were dried (MgSO4) then filtered and concentrated under reduced pressure to give a light-yellow solid. Recrystallisation (isopropanol) of this material afforded the title compound CP30218 (340 mg, 89%) as pale-yellow crystals, m.p. 105.0-105.7° C.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 3 h
  3. temperaturethen cooled
  4. customthe solvent evaporated under reduced pressure
  5. customThe ensuing residue was partitioned between CH2Cl2 (10 mL) and H2O (10 mL)
  6. extractionThe separated aqueous fraction was extracted with CH2Cl2 (1×5.0 ml)
  7. dry with materialthe combined organic fractions were dried (MgSO4)
  8. filtrationthen filtered
  9. concentrationconcentrated under reduced pressure
  10. customto give a light-yellow solid
  11. customRecrystallisation (isopropanol) of this material

Sources & evidence

ORD record
ord-20d13991690f42f4b83fbf3c2b02462a
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Linked notes

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