Ethanol → (6-Methoxy-naphthalen-2-ylmethylene)-methyl-amine

HRID 1357248Notes

Reaction equation

HRID 1357248 reaction equation
[CH3:1][NH2:2].C(O)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([CH:18]=O)[CH:12]=[CH:11]2.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([CH:18]=[N:2][CH3:1])[CH:12]=[CH:11]2

Participants

6

Reactant 4

HCID 702EthanolHCID 6329MethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 769916-Methoxy-2-naphthaldehyde

Product 1

HCID 18505302(6-Methoxy-naphthalen-2-ylmethylene)-methyl-amineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of an 8.03M solution of methylamine in ethanol (67 mL, 537 mmol) and 50 mL of methylene chloride was added dropwise under nitrogen to a mixture of 6-methoxy-naphthalene-2-carbaldehyde (20 g, 107.4 mmol), magnesium sulfate (20 g) and 200 mL of methylene chloride. The mixture stirred at room temperature under nitrogen for 17 h. The MgSO4 was removed by filtration and the solvent was removed under reduced pressure to give (6-methoxy-naphthalen-2-ylmethylene)-methyl-amine (20.59 g, 96%) as a yellow solid, mp 109-110° C.

Workup

  1. customThe MgSO4 was removed by filtration
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-81b10f073eaf4e198285c0f22af7fa90
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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