Methylamine → (5-Bromo-6-methoxy-naphthalen-2-ylmethylene)-methyl-amine

HRID 1357269Notes

Reaction equation

HRID 1357269 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH:16]=O)=[CH:9]2.[O-]S([O-])(=O)=O.[Mg+2]>C(O)C.C(Cl)Cl>[Br:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH:16]=[N:2][CH3:1])=[CH:9]2

Participants

6

Reactant 3

HCID 6329MethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 185053535-Bromo-6-methoxy-2-naphthaldehyde

Product 1

HCID 18505272(5-Bromo-6-methoxy-naphthalen-2-ylmethylene)-methyl-amineYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Methylamine (2.35 mL of an 8.03 M solution in ethanol, 18.8 mmol) in 5 mL of methylene chloride was added under nitrogen dropwise over 5 minutes to a mixture of 5-bromo-6-methoxy-naphthalene-2-carbaldehyde (1.00 g, 3.77 mmol), prepared in the previous step, and 3 g of anhydrous MgSO4 in 20 mL of methylene chloride at room temperature. After the addition the reaction was stirred at room temperature for 21 h (overnight). The reaction was filtered and the filtrate concentrated under reduced pressure to give (5-bromo-6-methoxy-naphthalen-2-ylmethylene)-methyl-amine (1.05 g, 100%) as a light tan solid, mp 105-107° C.

Workup

  1. additionAfter the addition the reaction
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8fe178240dcc498fb367cd926d88fb0a
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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