Hydrochloric Acid → 2-Chloro-5-(6-methylpyridin-3-yl)benzoic acid

HRID 456868Notes

Reaction equation

HRID 456868 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[CH:7]=[CH:6][C:5]=1[Cl:17].Cl>[OH-].[K+]>[Cl:17][C:5]1[CH:6]=[CH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[CH:9][C:4]=1[C:3]([OH:18])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 588181752-Chloro-5-(6-methyl-pyridin-3-yl)-benzoic acid methyl ester

Product 1

HCID 184386612-Chloro-5-(6-methylpyridin-3-yl)benzoic acidYield 122.6%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of 2-chloro-5-(6-methyl-pyridin-3-yl)-benzoic acid methyl ester (146 mg, 0.56 mmol) in methanolic potassium hydroxide (2.24 mL, 1M) was stirred at 80° C. for 16 h. The reaction mixture was acidified (pH 3) with 1N HCl and concentrated in vacuo. The residue was shaken thoroughly with methanol and filtered. The filtrate was concentrated in vacuo to afford the title compound (170 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2974450276e0455aae095174e3d9beae
Source dataset
uspto-grants-2007_03
Patent number
US07186742B2

Reaction notes

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