Methanesulfonyl chloride → HCID 69543249, compound

HRID 1776654Notes

Reaction equation

HRID 1776654 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH3:13][S:14]([NH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 7015521Ethyl 2-aminopyridine-4-carboxylate

Product 1

HCID 69543249HCID 69543249, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 2-aminoisonicotinate (1 g, 6.02 mmol) in dry pyridine (20 ml), methanesulfonyl chloride (0.938 ml, 12.04 mmol) was added at room temperature, and the resulting solution was stirred for 3 hours. Pyridine was evaporated and the residue was triturated with water (20 ml). The solid was collected by filtration and dried affording ethyl 2-(methylsulfonamido)isonicotinate as a light brown powder (1.3 g, 5.32 mmol, 88% yield, MS/ESI+ 245.2 [MH]+).

Workup

  1. customPyridine was evaporated
  2. customthe residue was triturated with water (20 ml)
  3. filtrationThe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-7d755800847c425ca847c9ee7411eb0d
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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