Veratraldehyde → N-[(3,4-Dimethoxyphenyl)methylidene]hydroxylamine

HRID 1838271Notes

Reaction equation

HRID 1838271 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[NH2:13][OH:14].Cl.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[N:13][OH:14])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 8419VeratraldehydeHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 16577N-[(3,4-Dimethoxyphenyl)methylidene]hydroxylamineYield 7,154.4%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

After dissolving 3,4-dimethoxybenzaldehyde (1.00 g, 0.081 mmol) in 60 mL of ethyl alcohol/water (1/1, v/v) solution, H2NOH HCl (0.54 g, 7.823 mmol) was added. While stirring the reaction mixture, Na2CO3 (0.83 g, 7.823 mmol) was added slowly at below 0° C. The reaction was continued for 1 hr in an oil bath preheated to 60-65° C. After the reaction was completed, 1.05 g (96.4%) of the target product was obtained by extracting with ethyl acetate, drying over anhydrous MgSO4 and removing the solvent under reduced pressure.

Workup

  1. additionwas added slowly at below 0° C
  2. custompreheated to 60-65° C

Sources & evidence

ORD record
ord-6a098c5249ff4df9a1180c5efc6c3211
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

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