1-(3-Hydroxy-4-methoxyphenyl)ethanone → 4-[[(E)-1-(3-hydroxy-4-methoxyphenyl)ethylideneamino]oxymethyl]benzonitrile

HRID 41939

Reaction equation

HRID 41939 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.[C:14]([C:16]1[CH:24]=[CH:23][C:19]([CH2:20][O:21][NH2:22])=[CH:18][CH:17]=1)#[N:15]>>[C:14]([C:16]1[CH:24]=[CH:23][C:19]([CH2:20][O:21]/[N:22]=[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:18][CH:17]=1)#[N:15]

Participants

3

Reactant 2

HCID 956931-(3-Hydroxy-4-methoxyphenyl)ethanoneHCID 19692695113211-35-1

Product 1

HCID 251004114-[[(E)-1-(3-hydroxy-4-methoxyphenyl)ethylideneamino]oxymethyl]benzonitrileYield 51%

Procedure

Acetophenone 12 (30 mg, 0.181 mmol) was condensed with O-(4-cyanobenzyl)hydroxylamine hydrochloride (35) (37 mg, 0.200 mmol) according to the general procedure II-B defined above. After being heated for 3 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing solid was filtered off and washed with cold isopropanol (3.0 mL) to afford the title compound CP30283 (27 mg, 51%) as a white solid, m.p. 125.9-129.7° C.

Workup

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

Sources & evidence

ORD record
ord-046a4e99e2c84c21b7473af2469c6e6d
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Linked notes

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