Hydrochloric Acid → HCID 21882727, compound

HRID 722048Notes

Reaction equation

HRID 722048 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH2:10][C:11]([O:13]C)=[O:12])[CH:4]=1.[OH-].[Na+].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21882722Methyl 3-(4-methoxypyridin-2-yl)propanoate2×

Product 1

HCID 21882727HCID 21882727, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

41.95 g of methyl 3-(4-methoxypyridin-2-yl)propionate (starting material A2) are dissolved in 700 ml of tetrahydrofuran, and 217 ml of 1N sodium hydroxide solution are added. The mixture is stirred at room temperature until no more starting material is detectable by thin-layer chromatography (TLC). The mixture is neutralized using 217 ml of 1N hydrochloric acid solution, evaporated to dryness using a rotary evaporator and dried under high vacuum. The colorless residue is ground and extracted four times with dichloromethane/methanol (9:1). The combined extracts are evaporated to dryness. This gives 33.2 g of the title compound as a colorless powder of m.p. 131–132° C. The mass spectrum shows the molecular peak MH+ at 182 Da.

Workup

  1. customevaporated to dryness
  2. customa rotary evaporator
  3. customdried under high vacuum
  4. extractionextracted four times with dichloromethane/methanol (9:1)
  5. customThe combined extracts are evaporated to dryness

Sources & evidence

ORD record
ord-8f81c94161ae4fa6b9a98235e9fee118
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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