3-Chloro-4-hydroxy-5-methoxybenzaldehyde → 2-Cyano-3-(3-chloro-4-hydroxy-5-methoxyphenyl) propenanilide

HRID 439554Notes

Reaction equation

HRID 439554 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[C:13]([CH2:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17])#[N:14]>C(O)C.N1CCCCC1>[C:13]([C:15](=[CH:7][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[C:3]([OH:12])=[C:2]([Cl:1])[CH:9]=1)[C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17])#[N:14]

Participants

5

Reactant 2

HCID 296223-Chloro-4-hydroxy-5-methoxybenzaldehydeHCID 69296Acetamide, 2-cyano-N-phenyl-

Product 1

HCID 541812382-Cyano-3-(3-chloro-4-hydroxy-5-methoxyphenyl) propenanilideYield 74.1%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-chlorovanillin (728 mg, 3.9 mmol) and cyanoacetanilide (625 mg, 3.9 mmol) in ethanol (20 ml) were added 3 drops of piperidine, and the resulting mixture was refluxed for 2 hours. After cooling to room temperature, the resulting solid was filtered and washed with ethanol: water (1: 1) to give the objective 2-cyano-3-(3-chloro-4-hydroxy-5-methoxyphenyl) propenanilide (950 mg, 74% in yield).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hours
  2. filtrationthe resulting solid was filtered
  3. washwashed with ethanol: water (1: 1)

Sources & evidence

ORD record
ord-ab545d1684904c21bbf62432b3ba8d21
Source dataset
uspto-grants-1996_05
Patent number
US05514711

Reaction notes

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