Hydrochloric Acid → 2-Chloro-6-[methyl(methylsulfonyl)amino]isonicotinic acid

HRID 2426795Notes

Reaction equation

HRID 2426795 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])[N:11]=1)[C:5]([O:7]C)=[O:6].C1COCC1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])[N:11]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86612064Methyl 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinate

Product 1

HCID 167483252-Chloro-6-[methyl(methylsulfonyl)amino]isonicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinate (2 g, 7.18 mmol) in 1:1 THF:MeOH (60 mL) added a NaOH (9.3 mL, 9.3 mmol, 1N). The reaction mixture was stirred at rt for 0.5 h, acidified to pH 3-4 with 1N HCl, extracted with dichloromethane (×2), dried over sodium sulfate and concentrated in vacuo to provide 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinic acid as a white solid. 1H NMR (400 MHz, CD3OD) δ 7.88 (s, 1H), 7.63 (s, 1H), 3.39 (s, 3H), 3.13 (s, 3H).

Workup

  1. extractionextracted with dichloromethane (×2)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-597d1bac0f744f7089eca8f84dbc1374
Source dataset
uspto-grants-2011_06
Patent number
US07968571B2

Reaction notes

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