Pyridine → HCID 22636441, compound

HRID 2415758Notes

Reaction equation

HRID 2415758 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[C:6]([C:8]([NH2:10])=O)[O:5][N:4]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:7]=[C:6]([C:8]#[N:10])[O:5][N:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 22636528HCID 22636528, compound

Product 1

HCID 22636441HCID 22636441, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Methoxy-5-isoxazolecarboxamide (J. Chem Soc. 1968, 172) (1.0 g, 7.0 mmol) was dissolved in dichloromethane (20 mL), cooled to 0° C. then pyridine (1.1 mL, 14 mmol) and trifluoroacetic anhydride (1.0 mL, 7.4 mmol) were added and the reaction was stirred at 0° C. for 40 minutes. The mixture was diluted with dichloromethane (10 mL) and then washed with 5% aqueous citric acid solution (3×20 mL). The combined organic extracts were dried (Na2SO4), and the solvent was removed in vacuo to give the title compound as a yellow oil (0.69 g).

Workup

  1. washwashed with 5% aqueous citric acid solution (3×20 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3d2cd1918c7f44d0942c5b4072ee5e77
Source dataset
uspto-grants-2004_11
Patent number
US06821972B2

Reaction notes

Loading…