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

HRID 1944572Notes

Reaction equation

HRID 1944572 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 (90.2 g, 323.6 mmol) in 1:1 THF:MeOH (1 L) was added a NaOH (388 mL, 388 mmol, 1N). The reaction mixture was stirred at rt for 2 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 (intermediate 4.2c.1) 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-6073d8546a8740418e162675cff1f6bc
Source dataset
uspto-grants-2013_03
Patent number
US08394837B2

Reaction notes

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