Phosphorus oxychloride → 2-Methoxy-6-methylpyridine

HRID 262478Notes

Reaction equation

HRID 262478 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:20][O-].[Na+]>>[CH3:20][O:8][C:6]1[N:7]=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 767726-Methylpyridin-2-olHCID 10942334Sodium Methoxide

Product 1

HCID 53247732-Methoxy-6-methylpyridine

Procedure

Successive treatment of 6-methyl-2-pyridone with a mixture of phosphoryl chloride and phosphorus pentachloride, and sodium methoxide gives 6-methoxy-2-methylpyridine which may be converted into 2-bromomethyl-6-methoxypyridine with N-bromosuccinimide. Substitution of 2-bromomethyl-6-methoxypyridine for 2-chloromethyl-3-methoxypyridine in the general procedure of Example 1(iii)-(v) leads to the preparation of N-cyano-N'-methyl-N"-[2-((6-methoxy-2-pyridyl)methylthio)ethyl]guanidine.

Sources & evidence

ORD record
ord-c453b085b3064233a29d2e8074579979
Source dataset
uspto-grants-1979_05
Patent number
US04154838

Reaction notes

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