p-Toluenesulfonic acid → HCID 15350007, compound

HRID 2120124Notes

Reaction equation

HRID 2120124 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-c02890ac9397424b8baa436d474eb2a6
Source dataset
uspto-grants-2004_02
Patent number
US06689781B2

Reaction notes

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