Hydrochloric Acid → 3-(5-Methylpyridin-2-yl)-5-(methylsulfonyl)benzoic acid

HRID 1845234Notes

Reaction equation

HRID 1845234 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:17]=2)[C:11]([O:13]C)=[O:12])=[N:6][CH:7]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].Cl>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:17]=2)[C:11]([OH:13])=[O:12])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 17749109Barium hydroxide, octahydrateHCID 58187970Methyl 3-(5-methylpyridin-2-yl)-5-(methylsulfonyl)benzoate

Product 1

HCID 581881503-(5-Methylpyridin-2-yl)-5-(methylsulfonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a round-bottom flask were charged methyl 3-(5-methylpyridin-2-yl)-5-(methylsulfonyl)benzoate (0.60 g, 1.96 mmol), barium hydroxide octahydrate (1.23 g, 3.90 mmol) and methanol (50 mL). The mixture was stirred at room temperature until the completion of the reaction. The mixture was acidified with HCl (2M ethyl ether solution, 20 mL). The mixture was concentrated to afford a mixture of the desired product and BaCl2 as a white solid (1.4 g, 40% purity). LC-MS: 291.5 [M+1]; 1H NMR (400 MHz, DMSO-d6): 8.90 (s, 1H), 8.80 (d, J=1.7 Hz, 1H), 8.63 (s, 1H), 8.43 (d, J=1.5 Hz, 1H), 8.16 (d, J=8.1 Hz, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.64-7.55 (m, 1H), 3.38 (s, 3H), 2.40 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto afford

Sources & evidence

ORD record
ord-9fff0c0f6cf747b785d084ea7671b788
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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