Dichloromethane → 2-Acetamido-5-chloropyridine

HRID 486249Notes

Reaction equation

HRID 486249 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].P([O-])([O-])(O)=O.[Na+].[Na+].[Cl:18]CCl.ClCl>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:18])=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24203Sodium Phosphate, DibasicHCID 24526ChlorineHCID 729292-Acetamidopyridine

Product 1

HCID 7986532-Acetamido-5-chloropyridineYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 300 ml of water, 13.6 g (0. lmol) of 2-acetamidopyridine (Id) was dissolved. To this solution, 35.5 g (0.25 mol) of disodium hydrogenphosphate and 100 ml of dichloromethane were added in this order. While this mixture was stirred, 8.0 g (0.11 mol) of chlorine was introduced thereto at 0° C. for 30 minutes. Then the mixture was further stirred at the same temperature for 2 hours. After the mixture was brought back to room temperature, it was separated into a water layer and an extract layer. Thereafter, the water layer was further extracted with 100 ml of dichloromethane and then washed with saturated brine. The resulting extract layer was dehydrated by sodium sulfate anhydride. When dichloromethane was evaporated off, 16.0 g (yield: 94.0%) of 2-acetamido-5-chloropyridine (IIj) was obtained as a pale brown crystal.

Workup

  1. stirringThen the mixture was further stirred at the same temperature for 2 hours
  2. customwas brought back to room temperature
  3. customit was separated into a water layer
  4. extractionThereafter, the water layer was further extracted with 100 ml of dichloromethane
  5. washwashed with saturated brine
  6. extractionThe resulting extract layer
  7. customWhen dichloromethane was evaporated off

Sources & evidence

ORD record
ord-e72657f8f6e14059b549fc264a50cd97
Source dataset
uspto-grants-1994_03
Patent number
US05290943

Reaction notes

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