Methyl 3-methyl-4-pyridinecarboxylate → 1-Amino-4-(methoxycarbonyl)-3-methylpyridinium 2,4,6-trimethylbenzenesulfonate

HRID 1802153Notes

Reaction equation

[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH2:13])(=[O:11])=[O:10].[CH3:15][C:16]1[CH:25]=[N:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]>ClCCl.C(OCC)C>[CH3:8][C:3]1[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:14])[C:2]=1[S:9]([O-:12])(=[O:11])=[O:10].[NH2:13][N+:24]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([CH3:15])[CH:25]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To an ice-cooled suspension (white) of O-(mesitylsulfonyl)hydroxylamine (1.75 g, 8.14 mmol) in dichloromethane (10 ml) is dropwise added a solution of methyl 3-methylisonicotinate (1.23 g, 8.14 mmol) in dichloromethane (3 ml). After the addition is completed, the resulting light yellow solution is stirred for 3 hours at 25° C. The solution is cooled to 0° C. and diluted with diethyl ether until a white solid precipitates. The suspension is stirred for 1 hour and the solid is collected by filtration, washed with ether and dried affording 1-amino-4-(methoxycarbonyl)-3-methylpyridinium 2,4,6-trimethylbenzenesulfonate (2.41 g, 80.8%) as a white solid. MS: m/z=167.2 (M+).

Workup

additionAfter the addition
temperatureThe solution is cooled to 0° C.
customprecipitates
stirringThe suspension is stirred for 1 hour
filtrationthe solid is collected by filtration
washwashed with ether
customdried

Sources & evidence

ORD record: ord-4dae7a6f8f3840f68d94f126ebf2f913
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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