Sodium Hydroxide → HCID 59255058, compound

HRID 1809350Notes

Reaction equation

HRID 1809350 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([O:15]CC)=[O:14])[C:5](=[O:12])[N:6]([CH:9]([CH3:11])[CH3:10])[C:7]=1[CH3:8].[OH-].[Na+]>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=[O:14])[C:5](=[O:12])[N:6]([CH:9]([CH3:11])[CH3:10])[C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59255055HCID 59255055, compound

Product 1

HCID 59255058HCID 59255058, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 5-chloro-1-isopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate as prepared in 1(6) (203 mg, 0.79 mmol) in tetrahydrofuran (2 mL) and methanol (2 mL) was added 2N sodium hydroxide aqueous solution (2 mL) at room temperature, and the mixture was stirred at room temperature for 16 h. Then, the solvent was removed in vacuo. The residue was diluted with water (30 mL), acidified with 2N hydrochloric acid aqueous solution (pH˜2) and extracted with dichloromethane (50 mL×3). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to give 171 mg (94%) of the title compound as a white solid.

Workup

  1. customThen, the solvent was removed in vacuo
  2. additionThe residue was diluted with water (30 mL)
  3. extractionextracted with dichloromethane (50 mL×3)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-184aaf80cc7a410eac8c77c0ce5c3303
Source dataset
uspto-grants-2013_01
Patent number
US08362038B2

Reaction notes

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