Hydrochloric Acid → 5-Chloro-4-cyclobutylmethoxy-pyridine-2-carboxylic acid

HRID 1480053Notes

Reaction equation

HRID 1480053 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH:13]2[CH2:16][CH2:15][CH2:14]2)[C:8]([Cl:17])=[CH:7][N:6]=1)=[O:4].[OH-].[Na+].Cl.C(OCC)(=O)C>C1COCC1>[Cl:17][C:8]1[C:9]([O:11][CH2:12][CH:13]2[CH2:16][CH2:15][CH2:14]2)=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 902043845-Chloro-4-cyclobutylmethoxy-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 902036505-Chloro-4-cyclobutylmethoxy-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloro-4-cyclobutylmethoxy-pyridine-2-carboxylic acid methyl ester (339 mg, 1.33 mmol) in THF (10 mL) was added sodium hydroxide solution (2.65 mL, 1 N). The resulting solution was stirred at room temperature for 2 hours, and afterwards acidified with hydrochloric acid (10 mL, 1N) and poured into ethyl acetate (50 mL). The phases were separated and the water phase was extracted with additional ethyl acetate; the organic portions were combined, dried over Na2SO4, filtered and concentrated. The crude material (286 mg, 89%) a white solid, was sufficiently pure to be used in the next step without further purification. MS (ESI, m/z): 240.1 (M−H−).

Workup

  1. customThe phases were separated
  2. extractionthe water phase was extracted with additional ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto be used in the next step without further purification

Sources & evidence

ORD record
ord-d2d2d5ebff95497da11d1083e8cc221c
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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