Dichloroacetic Acid → HCID 54724182, compound

HRID 1867023Notes

Reaction equation

HRID 1867023 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]1=[O:13].[I:17]N1C(=O)CCC1=O.ClC(Cl)C(O)=O>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([I:17])[C:7]1=[O:13]

Participants

5

Reactant 3

HCID 6597Dichloroacetic AcidHCID 120273N-IodosuccinimideHCID 54724162HCID 54724162, compound

Product 1

HCID 54724182HCID 54724182, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1-(3-fluorobenzyl)-4-hydroxypyridin-2(1H)-one (1.1 g, 5 mmol) in acetonitrile (15 mL) was added N-iodosuccinimide (1.1 g, 5.5 mmol) along with a ca. amount of dichloroacetic acid (0.1 mL). The reaction mixture stirred at room temperature for 1 hour under nitrogen. The mixture was chilled in an ice bath and filtered cold with fresh MeCl2. The beige solid was dried to afford the desired iodinated intermediate (1.21 g, 69%). ES-LRMS m/z 346.

Workup

  1. temperatureThe mixture was chilled in an ice bath
  2. filtrationfiltered cold with fresh MeCl2
  3. customThe beige solid was dried
  4. customto afford the

Sources & evidence

ORD record
ord-dce047879a5148b7bccca72715b1a0db
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

Loading…