1,2-Dichloroethane → 2-Chloro-4-methyl-5-nitropyridine

HRID 508477Notes

Reaction equation

HRID 508477 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4](O)[CH:3]=1.[Cl:12]CCCl.[Cl-].[P+]=O>CN(C=O)C>[Cl:12][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 178429283HCID 178429283, compoundHCID 178527006HCID 178527006, compound

Product 1

HCID 3453642-Chloro-4-methyl-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A 100 ml three-necked round-bottomed flask equipped with a magnetic bar, a thermometer, a dropping funnel and a reflux condenser is charged with 4-methyl-5-nitro-pyridin-2-ol (5.0 g), and 1,2-dichloroethane (30 ml). Phosphorous oxide chloride (3.6 ml) is added dropwise. Into this mixture DMF (2.5 ml) is added dropwise at ambient temperature. The reaction mixture is heated at 70° C. under stirring for 0.5 hours. After cooling the mixture to ambient temperature, it is concentrated in vacuo at 50° C., to obtain a brown oily gum. Purification of this gum by flash chromatography over silica gel with hexane/ethyl acetate 7:3 (v:v) gives 4.91 g of the compound as a light yellow solid (MP: 35-38° C.).

Workup

  1. customA 100 ml three-necked round-bottomed flask equipped with a magnetic bar
  2. temperatureAfter cooling the mixture to ambient temperature
  3. concentrationit is concentrated in vacuo at 50° C.
  4. customto obtain a brown oily gum
  5. customPurification of this gum by flash chromatography over silica gel with hexane/ethyl acetate 7:3 (v:v)

Sources & evidence

ORD record
ord-d4f535cba7424440a7037d8967b849b4
Source dataset
uspto-grants-2015_08
Patent number
US09096525B2

Reaction notes

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