N-methyl-2-pyrrolidone → 2-Chloro-6(dichloromethyl)pyridine

HRID 615436Notes

Reaction equation

HRID 615436 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](Cl)([Cl:10])[Cl:9])[N:3]=1.CN1CCCC1=O.COP([O-])OC.[OH-].[Na+]>O.N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([Cl:10])[Cl:9])[N:3]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium Hydroxide2×HCID 16004NitrapyrinHCID 21884954Dimethylphosphite

Product 1

HCID 1741112-Chloro-6(dichloromethyl)pyridineYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

In a stirred reaction vessel was placed 2.31 grams (0.010 mole) of 2-chloro-6-(trichloromethyl)pyridine, 20 ml of N-methylpyrrolidone and 1.35 grams (0.011 mole) of dimethylphosphite. The mixture was heated for about 21/2 hours. During this period, 50 percent aqueous sodium hydroxide was slowly added to maintain the pH slightly basic. At the end of the reaction period, there was 1% of the pyridine starting material remaining. Additionally, it was found that 0.0225 mole of the aqueous sodium hydroxide had been added. The reaction mixture was poured into water, extracted with methylene chloride, dried and the methylene chloride removed by evaporation, to yield 1.6 grams (80% of theoretical) of crude 2-chloro-6-(dichloromethyl)pyridine.

Workup

  1. customIn a stirred reaction vessel
  2. temperatureThe mixture was heated for about 21/2 hours
  3. waitDuring this period
  4. temperatureto maintain the pH slightly basic
  5. customAt the end of the reaction period, there
  6. additionhad been added
  7. extractionextracted with methylene chloride
  8. customdried
  9. customthe methylene chloride removed by evaporation

Sources & evidence

ORD record
ord-a70934c0ad1045e7b726224308af545a
Source dataset
uspto-grants-1985_02
Patent number
US04499277

Reaction notes

Loading…