Hydrochloric Acid → HCID 86612302, compound

HRID 253160Notes

Reaction equation

HRID 253160 reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:16])[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=1.Cl>CO.[Pd]>[ClH:1].[NH2:15][CH2:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[O:7][CH2:6][CH2:5][C:4]([O:3][CH3:2])=[O:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66845678HCID 66845678, compound

Product 1

HCID 86612302HCID 86612302, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.8 g (3.9 mmol) of the 3-(3-cyanophenoxy)propanoic acid methyl ester hydrochloride are dissolved in 20 ml of methanol. 0.4 ml of hydrochloric acid 10 N are added then, under an inert atmosphere, 100 mg of palladium on carbon. The mixture is agitated under a hydrogen atmosphere at ambient temperature and atmospheric pressure. The catalyst is eliminated by filtration, then the filtrate is concentrated under reduced pressure. The residue is recovered using toluene and evaporation is performed again. The product is recrystallised in a methanol/ethyl ether mixture (10/50; v/v), and dried under a vacuum. The expected product is obtained in the form of a white solid with a yield of 84%.

Workup

  1. filtrationThe catalyst is eliminated by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is recovered
  4. customtoluene and evaporation
  5. customThe product is recrystallised in a methanol/ethyl ether mixture (10/50; v/v)
  6. customdried under a vacuum

Sources & evidence

ORD record
ord-c74776abe61c424f93dfa441fcff8342
Source dataset
uspto-grants-2011_01
Patent number
US07872021B2

Reaction notes

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