Hydrochloric Acid → 3-(Pyridin-4-yl)propanoic acid

HRID 2217757Notes

Reaction equation

HRID 2217757 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([O:11]CC)=[O:10])=[CH:3][CH:2]=1.[OH-].[K+].Cl>O.CCO>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 12229233Ethyl isonicotinylacetate

Product 1

HCID 2332433-(Pyridin-4-yl)propanoic acidYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-pyridin-4-ylpropanoate (Method 7; 103.1 g, 576 mmol) in water (400 ml) and EtOH (20 ml) at room temperature was added potassium hydroxide (60 g, 1600 mmol). After 18 hours hydrochloric acid (100 ml) was added to give a white solid 62.8 g (73%). NMR (300 MHz) 8.38 (d, 2H), 7.21 (d, 2H), 2.70 (t, 2H), 2.52 (t, 2H); m/z 152.2.

Sources & evidence

ORD record
ord-5d788c62fce741e79e8a006ca49f4704
Source dataset
uspto-grants-2008_08
Patent number
US07408064B2

Reaction notes

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