Sulfuric Acid → 2,4-Dichloro-6-methylnicotinic acid

HRID 2214996Notes

Reaction equation

HRID 2214996 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([Cl:13])[CH:5]=[C:4]([CH3:14])[N:3]=1.[OH-].[Na+].OS(O)(=O)=O>O.CO>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([Cl:13])[CH:5]=[C:4]([CH3:14])[N:3]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 604813Ethyl 2,4-dichloro-6-methylnicotinate

Product 1

HCID 8204052,4-Dichloro-6-methylnicotinic acidYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of commercially available (Maybridge) ethyl 2,4-dichloro-6-methylpyridine-3-carboxylate (1.0 g, 4.3 mmol) and NaOH (342 mg, 8.6 mmol) in water (1.7 mL) and MeOH (1.5 mL) was heated to 80° C. for 4 h. The mixture was acidified using 50% H2SO4 and filtered. The solid was washed with cold water and dried to give of 2,4-dichloro-6-methylpyridine-3-carboxylic acid (582 mg, 66%): LCMS RT: 0.70 min, MH+: 206.2.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with cold water
  3. customdried

Sources & evidence

ORD record
ord-5c55d92b177444c2ac26aaf9d83d9046
Source dataset
uspto-grants-2006_09
Patent number
US07109196B2

Reaction notes

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