Lithium hydroxide, monohydrate → HCID 60097591, compound

HRID 2363936Notes

Reaction equation

HRID 2363936 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9]CC)=[O:8].O.[OH-].[Li+]>CCO.O>[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[CH:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15033186HCID 15033186, compound

Product 1

HCID 60097591HCID 60097591, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 2-amino-5-(pyridin-4-yl)thiophene-3-carboxylate (400 mg, 1.53 mmol) in EtOH (50 mL) was added a solution of lithium hydroxide monohydrate (256 mg, 6.1 mmol) in water (5 mL). The reaction mixture was heated to 80° C. for 2 hour. After removal of the solvent, the residue was dissolved in water and the organic materials were extracted with AcOEt (50 mL). The organic layer was discarded, and the aqueous layer was neutralized with 2N HCl aqueous solution to pH=5 or 6, upon with a precipitate formed. The solid was collected by filtration and dried to give the title compound (277 mg, 77%) as an orange solid:

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in water
  3. extractionthe organic materials were extracted with AcOEt (50 mL)
  4. customformed
  5. filtrationThe solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-50ccf5945dc84f88a4928b8f67f66d1a
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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