Dichloromethane → 5-Chloro-6-isopropoxynicotinic acid

HRID 2189764Notes

Reaction equation

HRID 2189764 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]([O:16]C(C)C)=[O:15])[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12].C(Cl)Cl>CO>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[CH:7]=[N:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 22985641Isopropyl 5-chloro-6-isopropoxynicotinate

Product 1

HCID 180705825-Chloro-6-isopropoxynicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (29.1 ml, 58.2 mmol) was added to a solution of 1-methylethyl 5-chloro-6-[(1-methylethyl)oxy]-3-pyridinecarboxylate (D30) (3 g, 11.64 mmol) in methanol (25 ml) and stirred at room temperature overnight. The solvent was evaporated before neutralising with 2M HCl and extracting with ether. It was then dried over magnesium sulfate and evaporated to give an impure white solid. Trituration with DCM gave the title compound as a pure white solid. MS (ES) C9H10ClNO3 requires 215, found 216 [M+H]+

Workup

  1. customThe solvent was evaporated
  2. extractionextracting with ether
  3. dry with materialIt was then dried over magnesium sulfate
  4. customevaporated
  5. customto give an impure white solid

Sources & evidence

ORD record
ord-42ccdb8741834b57afa605ba4447cd37
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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