Hydrochloric Acid → 2-[(6-Chloropyridin-3-yl)methyl]-2-methylmalonic acid

HRID 1714416Notes

Reaction equation

HRID 1714416 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:18])([C:14]([O:16]C)=[O:15])[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([CH3:18])([C:14]([OH:16])=[O:15])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59215199Dimethyl 2-[(6-chloropyridin-3-yl)methyl]-2-methylmalonate

Product 1

HCID 542838152-[(6-Chloropyridin-3-yl)methyl]-2-methylmalonic acidYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of dimethyl 2-[(6-chloropyridin-3-yl)methyl]-2-methylmalonate (10.85 g, 40 mmol) in THF (80 mL) was added a solution of lithium hydroxide monohydrate (5.7 g, 0.136 mol) in water (43 mL). The resulting mixture was stirred overnight at room temperature and then poured into water (300 mL). The pH was adjusted to less than 2 by the addition of concentrated HCl. The resulting mixture was extracted with ether (3×100 mL) and the ether extracts were combined, washed with brine (100 mL) and dried over anhydrous MgSO4. After a filtration, the solvent was evaporated to give 9.26 g of the product as a white solid in 95% yield: m.p. 168° C. (decomp.).

Workup

  1. extractionThe resulting mixture was extracted with ether (3×100 mL)
  2. washwashed with brine (100 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationAfter a filtration
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-515a8df1d73a45b6ae219d4c01d500e6
Source dataset
uspto-grants-2010_09
Patent number
US07795456B2

Reaction notes

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