Sodium Hydroxide → 5-Ethynylpyridin-2-amine

HRID 269082Notes

Reaction equation

HRID 269082 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9]C(C)(O)C)=[CH:4][CH:3]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[N:7][CH:6]=1)#[CH:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67000911HCID 67000911, compound

Product 1

HCID 219548275-Ethynylpyridin-2-amineYield 36.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-(6-amino-pyridin-3-yl)-2-methyl-but-3-yn-2-ol (example D.1 method 2 step 1) (22.5 g, 128 mmol) in toluene (500 mL) was refluxed in the presence of powdered NaOH (3.83 g, 96 mmol) for 16 h. The solvent was removed under reduced pressure to leave a brown residue which was purified by silica gel column chromatography with dichloromethane and ether, followed by trituration with heptane to give the title compound (5.5 g, 36%) (31.1 g, 100%) as light red solid. MS (EI) 118.1 [(M)+]; mp 143° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto leave a brown residue which
  3. customwas purified by silica gel column chromatography with dichloromethane and ether

Sources & evidence

ORD record
ord-4b7a81f9be0544cba8c8152ccc629879
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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