Hydrochloric Acid → HCID 70896531, compound

HRID 1619289Notes

Reaction equation

HRID 1619289 reaction equation
C([O:4][C:5]([C:7]1[C:12]([C:13]#[N:14])=[CH:11][C:10]([Br:15])=[CH:9][N:8]=1)=[O:6])(C)C.O.[OH-].[Li+].Cl>C1COCC1.O>[Br:15][C:10]1[CH:11]=[C:12]([C:13]#[N:14])[C:7]([C:5]([OH:6])=[O:4])=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68259684HCID 68259684, compound

Product 1

HCID 70896531HCID 70896531, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-bromo-3-cyano-pyridine-2-carboxylic acid isopropyl ester (70 mg, 0.26 mmol) in a mixture of THF (3 ml) and water (3 ml) was added lithium hydroxide monohydrate (32.75 mg, 0.78 mmol, 3 equiv.). The reaction mixture was stirred for 2 hours at 25° C. The mixture was acidified with 2N aqueous HCl solution (pH 5) and extracted with EtOAc (2×15 ml). The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to dryness to give 5-bromo-3-cyano-pyridine-2-carboxylic acid (45 mg, 76%) as a yellow solid which was used in next step without further purification.

Workup

  1. extractionextracted with EtOAc (2×15 ml)
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-f39d5b204f0142d7b2bc9d537663708d
Source dataset
uspto-grants-2014_07
Patent number
US08772300B2

Reaction notes

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