1-Methoxy-2-propanol → Pyridine, 2,3,5-trichloro-

HRID 1763243Notes

Reaction equation

HRID 1763243 reaction equation
COCC(O)C.Cl[C:8]1[N:13]=[C:12]([Cl:14])[C:11]([Cl:15])=[C:10](Cl)[C:9]=1[Cl:17].[OH-].[NH4+]>O.C1(C)C=CC=CC=1.[Zn]>[Cl:14][C:12]1[C:11]([Cl:15])=[CH:10][C:9]([Cl:17])=[CH:8][N:13]=1

Participants

7

Reactant 3

HCID 79001-Methoxy-2-propanolHCID 14923Ammonium HydroxideHCID 16584Pentachloropyridine2×

Product 1

HCID 27666Pyridine, 2,3,5-trichloro-Yield 164.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a 500 milliliter, 3-neck flask which was fitted with a reflux condenser, thermometer, stirrer and heater was added 100 milliliters of 1-methoxy-2-propanol, 25.1 grams (0.10 mole) of pentachloropyridine and 39.0 grams (0.60 gram atom) of zinc dust. The flask was heated, with stirring, to 90° C. until all the pentachloropyridine was dissolved. At this time, 100 milliliters of concentrated ammonium hydroxide was added over a 5 hour period. The pH of the mixture was ~12. The mixture was refluxed for 32 hours and the reaction mixture was diluted with two volumes of water and 100 milliliters of toluene. The mixture was filtered to remove insolubles. The toluene was removed by fractionation leaving 30.0 grams of crude 2,3,5-trichloropyridine as an amber-colored oil. Analysis by gas-liquid chromatography showed a yield of 2.1 grams of the desired product (12 percent of theoretical).

Workup

  1. customTo a 500 milliliter, 3-neck flask which was fitted with a reflux condenser
  2. temperatureThe flask was heated
  3. dissolutionwas dissolved
  4. temperatureThe mixture was refluxed for 32 hours
  5. filtrationThe mixture was filtered
  6. customto remove insolubles
  7. customThe toluene was removed by fractionation

Sources & evidence

ORD record
ord-d190ba956e554f28997ff2087e410686
Source dataset
uspto-grants-1978_09
Patent number
US04111938

Reaction notes

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