p-Toluenesulfonic acid → HCID 15350007, compound

HRID 1591804Notes

Reaction equation

HRID 1591804 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[CH2:9]([CH2:13][C:14](=O)[CH3:15])[C:10]([CH3:12])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]2[C:14]([CH3:15])=[CH:13][CH:9]=[C:10]2[CH3:12])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80352,5-HexanedioneHCID 661742-Amino-5-chloropyridine

Product 1

HCID 15350007HCID 15350007, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Amino-5-chloropyridine (10.0 g, 77 mmol), acetonyl acetone (8.8 g, 77 mmol) and a catalytic amount of p-toluenesulphonic acid in anhydrous toluene (250 ml) was heated to reflux for 5 h under Dean and Stark conditions. The solvent was-removed in vacuo, the residue slurried in hexane (250 ml), filtered through celite and the solvent removed in vacuo to give the title compound as a yellow oil (16.0 g): δH (CDCl3) 8.57 (1H, dd, J 2.7, 0.6 Hz), 7.78 (1H, dd, J 8.4, 2.7 Hz), 7.17 (1H, m, J 7.5, 0.5 Hz), 5.91 (2H, s), 2.14 (6H, s).

Workup

  1. temperatureto reflux for 5 h under Dean and Stark conditions
  2. customThe solvent was-removed in vacuo
  3. filtrationfiltered through celite
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e4690e3234414e57ae8c2c87ac0cebd0
Source dataset
uspto-grants-2007_11
Patent number
US07291645B2

Reaction notes

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