Hydrochloric Acid → 2-Chloro-6-[methyl(pyridin-3-ylsulfonyl)amino]isonicotinic acid

HRID 1944579Notes

Reaction equation

HRID 1944579 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([CH3:22])[S:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:14])[N:11]=1)[C:5]([O:7]C)=[O:6].CO.[OH-].[Na+].Cl>CCOC(C)=O.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]([CH3:22])[S:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:14])[N:11]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86616988Methyl 2-chloro-6-[methyl(pyridin-3-ylsulfonyl)amino]isonicotinate

Product 1

HCID 866169892-Chloro-6-[methyl(pyridin-3-ylsulfonyl)amino]isonicotinic acidYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-chloro-6-[methyl(pyridin-3-ylsulfonyl)amino]isonicotinate (3.12 g, 9.13 mmol) in 1:1 MeOH:THF (60 mL total) was added 1N NaOH solution (27 mL, 27.4 mmol). After 1 h, reaction was concentrated in vacuo. Reaction was diluted with EtOAc (100 mL) and acidified with 1N HCl (50 mL) solution. The aqueous solution was extracted with EtOAc (100 mL×3). The combined organics were washed with brine (100 mL), dried over Mg2SO4, filtered, and concentrated in vacuo to give 2.63 g (88%) of 2-chloro-6-[methyl(pyridin-3-ylsulfonyl)amino]isonicotinic acid as a white solid. LC/MS [M+H]+=328.1.

Workup

  1. customreaction
  2. concentrationwas concentrated in vacuo
  3. customReaction
  4. extractionThe aqueous solution was extracted with EtOAc (100 mL×3)
  5. washThe combined organics were washed with brine (100 mL)
  6. dry with materialdried over Mg2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f7761639fe047bf8a2bc87005dfa70a
Source dataset
uspto-grants-2013_03
Patent number
US08394837B2

Reaction notes

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