Hydrochloric Acid → Lithium Chloride

HRID 1752510Notes

Reaction equation

HRID 1752510 reaction equation
C[O:2][C:3]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[CH3:13])=[CH:7][N:6]=1)=[O:4].[Li+:16].[OH-].[ClH:18]>C1COCC1.O>[Cl:11][C:10]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=[C:8]([C:12]([F:14])([F:15])[CH3:13])[CH:9]=1.[Li+:16].[Cl-:18]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71271419HCID 71271419, compound

Product 2

HCID 433294Lithium ChlorideHCID 71271371HCID 71271371, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-5-(1,1-difluoro-ethyl)-pyridine-2-carboxylic acid methyl ester (272 mg, 1.154 mmol) in THF (6 ml) was added LiOH (30.4 mg, 1.27 mmol) in water (0.5 ml) and the mixture was stirred for 3.5 h. To the mixture was added 6N HCl (0.212 ml, 1.27 mmol) and the solvent was evaporated. The residue was taken up in toluene and evaporated (2×) to provide the title compound as colorless solid together with LiCl. This material was directly used in the coupling step without further purification.

Workup

  1. customthe solvent was evaporated
  2. customevaporated (2×)

Sources & evidence

ORD record
ord-1912f8d33bb443a682421f3b705d5443
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

Loading…