3-Hydroxyacetophenone → 3-[(E)-C-methyl-N-[(4-nitrophenyl)methoxy]carbonimidoyl]phenol

HRID 41932

Reaction equation

HRID 41932 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.Cl.[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([CH2:19][O:20][NH2:21])=[CH:17][CH:16]=1)([O-:14])=[O:13]>>[N+:12]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:8](/[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=2)\[CH3:9])=[CH:22][CH:23]=1)([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 84873-HydroxyacetophenoneHCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)

Product 1

HCID 251000943-[(E)-C-methyl-N-[(4-nitrophenyl)methoxy]carbonimidoyl]phenolYield 82%

Procedure

3′-Hydroxyacetophenone (24) (150 mg, 1.10 mmol) was condensed with compound 19 (248 mg, 1.21 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 resulting solid was filtered off and washed with cold isopropanol (3.0 mL) to afford the title compound CP30260 (257 mg, 82%) as a white solid, m.p. 123.6-125.3° C.

Workup

  1. temperatureAfter being heated for 3 h the reaction mixture
  2. temperaturewas cooled
  3. customthe solvent removed under reduced pressure
  4. filtrationThe resulting solid was filtered off
  5. washwashed with cold isopropanol (3.0 mL)

Sources & evidence

ORD record
ord-266b105a4a4f4cf9893712840d16ff93
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Linked notes

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