Methylamine → 4-Chloro-6-methyl-2-methylaminopyridine

HRID 2255918Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][NH2:11]>C(O)C>[Cl:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([NH:11][CH3:10])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2,4-dichloro-6-methylpyridine (7.0 g) (West German Patent DE 2162238) and 33% w/v methylamine in ethanol (25 ml) was heated in a sealed tube at 100° C. for 8 hours. The solvent was removed by evaporation and the residual solid was purified by flash chromatography (Merck 9385 Silica, 100 g), using as eluant first an increasing gradient [20%-100% v/v] of diethyl ether in petrol (b.p. 60°-80° C.) and then an increasing gradient of up to 5% v/v methanol in dichloromethane. There was thus obtained 4-chloro-6-methyl-2-methylaminopyridine (0.8 g, 12% yield), m.p. 69°-70° C.; NMR: 2.2-2.3(3H,s, CH3), 2.7-2.8(3H,s,NHCH3), 6.25(1H,s, pyridine-3H), 6.4(1H,s, pyridine-5H), 6.55-6.7(1H,br,NH).

Workup

customThe solvent was removed by evaporation
customthe residual solid was purified by flash chromatography (Merck 9385 Silica, 100 g)

Sources & evidence

ORD record: ord-27ab5f7bdb2745faa382f3784163ba52
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654298

Reaction notes

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