Lithium Hydroxide → 2-Chloro-6-(cyclopropylethynyl)nicotinic acid

HRID 2102909Notes

Reaction equation

HRID 2102909 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][CH:5]=[C:4]([C:13]#[C:14][CH:15]2[CH2:17][CH2:16]2)[N:3]=1.[OH-].[Li+]>CO.O>[Cl:1][C:2]1[N:3]=[C:4]([C:13]#[C:14][CH:15]2[CH2:17][CH2:16]2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57804191HCID 57804191, compound

Product 1

HCID 578041512-Chloro-6-(cyclopropylethynyl)nicotinic acidYield 64.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The ester was hydrolyzed as follows: Ethyl 2-chloro-6-(2-cyclopropylethynyl)pyridine-3-carboxylate (0.7 g, 2.8 mmol) and lithium hydroxide (0.4 g, 16.86 mmol) were refluxed in a mixture of 30 mL MeOH and 10 mL water. The mixture was cooled and the methanol was removed in vacuo. The remaining solution was acidified to pH 2 with 1M HCl at 0° C. The precipitate was filtered and dried to give 0.4 g (57%) of the title compound. m/z=222.4 (M+1).

Workup

  1. temperatureThe mixture was cooled
  2. customthe methanol was removed in vacuo
  3. customwas acidified to pH 2 with 1M HCl at 0° C
  4. filtrationThe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-71266e4606284115827a6a8dec1f847a
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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