Acetophenone → (E)-N-[(4-nitrophenyl)methoxy]-1-phenylethanimine

HRID 41927

Reaction equation

HRID 41927 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].Cl.[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([CH2:18][O:19][NH2:20])=[CH:16][CH:15]=1)([O-:13])=[O:12]>>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][O:19]/[N:20]=[C:1](/[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)\[CH3:2])=[CH:21][CH:22]=1)([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 7410AcetophenoneHCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)

Product 1

HCID 25100092(E)-N-[(4-nitrophenyl)methoxy]-1-phenylethanimineYield 77%

Procedure

Acetophenone (20) (150 mg, 1.25 mmol) was condensed with compound 19 (280 mg, 1.37 mmol) according to the general procedure II-A defined above. After heating the reaction mixture for 2 h it 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 CP30252 (258 mg, 77%) as a pale-yellow solid, m.p. 91.3-92.3° C.

Workup

  1. temperatureAfter heating the reaction mixture for 2 h it
  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-23a916c9fb6443c8ab25be0c5e823b60
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Linked notes

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