Methylamine → N-[(6-Chloro-3-pyridinyl)methylene]methanamine

HRID 249472Notes

Reaction equation

HRID 249472 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][CH:3]=1.[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:17][NH2:18].[O-]S([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[N:18][CH3:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 24436Sodium SulfateHCID 27640536-Chloropyridine-3-carbaldehyde

Product 1

HCID 53755856N-[(6-Chloro-3-pyridinyl)methylene]methanamineYield 68.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 30 ml of toluene, 0.8 g (5.7×10-3 moles) of 6-chloropyridine-3-aldehyde and 10 g of Na2SO4 were mixed and while the mixtures was stirred, a 40% aqueous solution of methylamine (1.4 g, 1.1×10-2 mole) was added dropwise over 30 minutes, followed by addition of 10 g of MgSO4. The mixture was allowed to stand at room temperature overnight, after which it was filtered. The filtrate was concentrated to give 0.6 g (yield 68%) of N-(6-chloro-3-pyridylmethylidene)methylamine as crystals.

Workup

  1. filtrationafter which it was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5ab3656127a34542bf8a4841857a2604
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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