Hydrochloric Acid → Pyridinium chloride

HRID 1448029Notes

Reaction equation

HRID 1448029 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.N1C=CC=CC=1.[Cl:15][C:16]1[C:21]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29]C)=[CH:20][CH:19]=[CH:18][N:17]=1>O>[ClH:15].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17]1[C:16]2[O:29][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10176127Pyridinium chlorideHCID 20381196HCID 20381196, compound

Product 2

HCID 10176127Pyridinium chlorideHCID 14294259[1,4]Benzodioxino[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Anhydrous pyridine hydrochloride is prepared by distillation to a temperature of 220° C. from a mixture of 42 g of pyridine and 50 ml of concentrated hydrochloric acid. Under a nitrogen atmosphere, the pyridine hydrochloride is allowed to cool to 100° C. and 5 g of 2-chloro-3-(2-methoxyphenoxy)pyridine is added and the mixture is refluxed 1 hour. The mixture is cooled and 200 ml of water is added. The mixture is extracted with 250 ml diethyl ether and the extracts are washed with 10 ml of concentrated ammonium hydroxide. The ether layer is dried and evaporated to yield the pyrido[2,3-B][1,4]benzodioxin, mp 95°-97° C., after sublimation at 0.1 mm pressure.

Workup

  1. temperaturethe mixture is refluxed 1 hour
  2. temperatureThe mixture is cooled
  3. extractionThe mixture is extracted with 250 ml diethyl ether
  4. washthe extracts are washed with 10 ml of concentrated ammonium hydroxide
  5. dry with materialThe ether layer is dried
  6. customevaporated

Sources & evidence

ORD record
ord-cf66c95b425b49f6b476ab7f78a0ecbb
Source dataset
uspto-grants-1979_12
Patent number
US04179506

Reaction notes

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