Benzylamine → Benzyl-(6-methoxy-naphthalen-2-ylmethylene)-amine

HRID 1357292Notes

Reaction equation

HRID 1357292 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([CH:21]=O)[CH:15]=[CH:14]2.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH2:1]([N:8]=[CH:21][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[CH:19][CH:20]=[C:11]([O:10][CH3:9])[CH:12]=2)[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 769916-Methoxy-2-naphthaldehyde

Product 1

HCID 18505309Benzyl-(6-methoxy-naphthalen-2-ylmethylene)-amineYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzylamine (0.57 mL, 5.37 mmol) in 5 mL of methylene chloride was added dropwise under nitrogen over 5 minutes to a mixture of 6-methoxy-naphthalene-2-carbaldehyde (1.0 g, 5.37 mmol) and anhydrous MgSO4 (3 g) in 20 mL of methylene chloride. The reaction stirred under nitrogen for 24 h (overnight). The MgSO4 was removed by filtration and the solvent removed under reduced pressure to give benzyl-(6-methoxy-naphthalen-2-ylmethylene)-amine (1.455 g, 98%) as an off-white solid, mp 115-117° C.

Workup

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

Sources & evidence

ORD record
ord-88c3bf9a50654e5097980b0c70eaf217
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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