Trifluoroacetic acid → HCID 19881175, compound

HRID 847357Notes

Reaction equation

HRID 847357 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[CH:4][CH:3]=1.[I:11]N1C(=O)CCC1=O.FC(F)(F)C(O)=O>C(O)(=O)C>[I:11][C:3]1[CH:4]=[C:5]([C:9]#[N:10])[C:6](=[O:8])[NH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 779193-Pyridinecarbonitrile, 1,2-dihydro-6-methyl-2-oxo-HCID 120273N-Iodosuccinimide

Product 1

HCID 19881175HCID 19881175, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 13.4 g (0.1 mole) of 1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile, 22.5 g (0.1 mole) of N-iodosuccinimide and 5 mL of trifluoroacetic acid in 250 mL of acetic acid was heated to reflux under argon for 4 hrs. The reaction was cooled and filtered to remove the crystalline precipitated product which was washed with water and ether and air dried to give 22.3 g (86%) of the 5-iodopyridinone as dense, light yellow needles, mp 260-264.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under argon for 4 hrs
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. customto remove the crystalline precipitated product which
  6. washwas washed with water and ether and air
  7. customdried

Sources & evidence

ORD record
ord-f8bc7608db02461fa7af9cde2e2604a7
Source dataset
uspto-grants-1992_08
Patent number
US05141931

Reaction notes

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