Hydrochloric Acid → HCID 21882727, compound

HRID 133100Notes

Reaction equation

HRID 133100 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 (compound F2) are dissolved in 700 ml of tetrahydrofuran, and 217 ml of 1N sodium hydroxide solution are added. The mixture is stirred at RT until no more starting material is detectable (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 332 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-38fd43f795b8436488c677f4a5a66bc6
Source dataset
uspto-grants-2008_06
Patent number
US07390819B2

Reaction notes

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