Hydrochloric Acid → 2-Chloro-5-iodo-3-methylpyridine

HRID 842040

Reaction equation

HRID 842040 reaction equation
[Cl:1]Cl.Cl.N[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][N:6]=1.N([O-])=O.[Na+]>O>[Cl:1][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24526ChlorineHCID 9595865-Iodo-3-methylpyridin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 226028192-Chloro-5-iodo-3-methylpyridineYield 14.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

At −10° C., 21.3 g of chlorine gas were introduced into a suspension of 146 g of 10% strength by weight hydrochloric acid and 23.4 g of 2-amino-3-methyl-5-iodopyridine [J. Org. Chem. (1995), p. 5356]. At about −50° C., a solution of 48.3 g of sodium nitrite in 120 ml of water was subsequently added dropwise. After about 2 hours of stirring at 0° C., the mixture was diluted with 1 l of water and extracted with methyl tert-butyl ether (MtBE). The organic phases were washed with NaHCO3 solution and water and then dried. Distillative removal of the solvent under reduced pressure and silica gel chromatography (cyclohexane/MtBE=1:10) gave 3.6 g of the product in the form of dark crystals.

Workup

  1. extractionextracted with methyl tert-butyl ether (MtBE)
  2. washThe organic phases were washed with NaHCO3 solution and water
  3. customdried
  4. customDistillative removal of the solvent under reduced pressure and silica gel chromatography (cyclohexane/MtBE=1:10)

Sources & evidence

ORD record
ord-7d5ef95bb24f494384acc870fba2e641
Source dataset
uspto-grants-2002_04
Patent number
US06372766B1

Linked notes

Loading…