Ethanol → N-[(2-methoxynaphthalen-1-yl)methylidene]hydroxylamine

HRID 651958Notes

Reaction equation

HRID 651958 reaction equation
C(O)C.[CH3:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH:16]=O.C([O-])(=O)C.[Na+].Cl.[NH2:24][OH:25]>O>[CH3:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH:16]=[N:24][OH:25]

Participants

6

Reactant 4

HCID 702EthanolHCID 793522-Methoxy-1-naphthaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 708036N-[(2-methoxynaphthalen-1-yl)methylidene]hydroxylamineYield 97.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 400 ml of ethanol and 180 ml of water were added 80 g (0.43 mole) of 2-methoxy-1-naphthaldehyde, 66 g (0.81 mole) of sodium acetate and 35.5 g (0.51 mole) of hydroxylamine hydrochloride, and the mixture was heated at reflux for 2 hours. After the reaction, the reaction mixture was added to 1 liter of water. The precipitated crystals were collected by filtration to give 85 g (0.42 mole) of 2-methoxy-1-naphthaldoxime.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customAfter the reaction
  4. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-ac2b684a0c544cb18038efc904bdc6e5
Source dataset
uspto-grants-1987_06
Patent number
US04670373

Reaction notes

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