Hydrochloric Acid → Lithium Chloride

HRID 1752493Notes

Reaction equation

HRID 1752493 reaction equation
C[O:2][C:3]([C:5]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]#[C:13][CH2:14][OH:15])=[CH:7][N:6]=1)=[O:4].[OH-].[Li+:17].[ClH:18]>C1COCC1>[NH2:11][C:10]1[C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=[C:8]([C:12]#[C:13][CH2:14][OH:15])[CH:9]=1.[Cl-:18].[Li+:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71271126HCID 71271126, compound

Product 2

HCID 433294Lithium ChlorideHCID 86689166HCID 86689166, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-5-(3-hydroxy-prop-1-ynyl)-pyridine-2-carboxylic acid methyl ester (297 mg, 1.44 mmol) in THF (10 ml) was added 1N lithium hydroxide and the mixture was vigorously stirred at room temperature for 4.5 h. To the mixture was added 4N HCl (0.47 ml, 1.87 mmol), after dilution with toluene the solvent was evaporated, the residue was suspended in toluene and evaporated (twice). The residue was suspended in TBME/hexane, filtered and the solid dried under reduced pressure at 50° C. to provide the title compound together with lithium chloride as a brown solid. The mixture was used for coupling reactions without further purification.

Workup

  1. customafter dilution with toluene the solvent was evaporated
  2. customevaporated (twice)
  3. filtrationfiltered
  4. customthe solid dried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-03c52520af3d4feebeb3835311b8c1b9
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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