Water → 2-Chloro-6(dichloromethyl)pyridine

HRID 615435Notes

Reaction equation

HRID 615435 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.[OH-].[Na+].P([O-])(OC)OC.O>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([Cl:10])[Cl:9])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 16004NitrapyrinHCID 21884954Dimethylphosphite

Product 1

HCID 1741112-Chloro-6(dichloromethyl)pyridineYield 71.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a reaction vessel fitted with a magnetic stirrer, 2.31 grams (10 mmole) of 2-chloro-6-(trichloromethyl)pyridine was dissolved in 25 ml of N-methylpyrrolidone. To this mixture was added 2.0 grams of 50% aqueous sodium hydroxide and 1.29 grams (10.2 mmole) of dimethyl phosphite. Within five minutes the temperature rose from 24° C. to 55° C. Analysis by glc indicated a ratio of 97.6/1.7 for reduced product to starting material. The reaction mixture was poured into 100 ml of water and the oil which separated was crystallized to form 1.4 grams of 2-chloro-6-(dichloromethyl)pyridine (mp 50°-53° C.). The yield was calculated to be 71% of theoretical.

Workup

  1. customIn a reaction vessel fitted with a magnetic stirrer
  2. customthe oil which separated
  3. customwas crystallized

Sources & evidence

ORD record
ord-7c7af9fa04ca4899b5a32a4ab6718d0b
Source dataset
uspto-grants-1985_02
Patent number
US04499277

Reaction notes

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