Methanol → 1-(3-chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxylic Acid

HRID 404568Notes

Reaction equation

HRID 404568 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH:12]=[C:11]([C:14]#N)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-:16].[Na+].C[OH:19]>C[Si](C)(C)C1C=C(C=CC=1)N>[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH:12]=[C:11]([C:14]([OH:19])=[O:16])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 583194961-(3-Chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carbonitrile2×

Product 1

HCID 219047271-(3-chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 124888833-(Trimethylsilyl)anilineSolvent

Procedure

A solution of 1-(3-chloropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carbonitrile (compound 23) in 1 20 ml of NaOH (5 g, 125 mmol) water solution and methanol (20 ml) (V/V=1:1) was heated to reflux, and stirred overnight. The reaction was washed by a HCl solution in an ice bath, and extracted by ethyl acetate. The organic layer was evaporated to give a crude product, which was purified using column chromatography to give the product.

Workup

  1. temperatureto reflux
  2. washThe reaction was washed by a HCl solution in an ice bath
  3. extractionextracted by ethyl acetate
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-3ae6ca62ab2741cca19f859dc1aa984f
Source dataset
uspto-grants-2014_06
Patent number
US08748610B2

Reaction notes

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