Sodium Hydroxide → 5-Chloro-6-isopropoxynicotinic acid

HRID 2189763Notes

Reaction equation

HRID 2189763 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([O:14]C(C)C)=[O:13])[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C(O)(C)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22985641Isopropyl 5-chloro-6-isopropoxynicotinate

Product 1

HCID 180705825-Chloro-6-isopropoxynicotinic acidYield 97.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

1-Methylethyl 5-chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylate (D30) (1.6 g, 6.21 mmol) in isopropanol (70 ml) and water (35.0 ml) was treated with 2N sodium hydroxide (6.21 ml, 12.42 mmol) and stirred for 3 hours to give a single product. Evaporated off the IPA, acidified with glacial acetic acid and extracted product into EtOAc (100 ml). Dried over MgSO4 and evaporated off the solvent to yield 1.30 g of the title compound as a white solid. MS (ES) C9H1035ClNO3 requires 215; found 214 (M−H+).

Workup

  1. customto give a single product
  2. customEvaporated off the IPA
  3. extractionextracted product into EtOAc (100 ml)
  4. dry with materialDried over MgSO4
  5. customevaporated off the solvent

Sources & evidence

ORD record
ord-607d014b10844986b5ff4ce964e3902a
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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