Water → HCID 20475368, compound

HRID 2295394Notes

Reaction equation

HRID 2295394 reaction equation
[CH3:1][C:2]1[C:3]([C:13]2[N+:14]([O-])=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:4][C:5]([CH2:8][O:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:7]=1.P(Cl)(Cl)Cl.O>C1C=CC=CC=1>[CH3:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:4][C:5]([CH2:8][O:9][C:10](=[O:12])[CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24387Phosphorus trichlorideHCID 20475370HCID 20475370, compound

Product 1

HCID 20475368HCID 20475368, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
23 °C

Procedure

2.1 g (8.1 mmols) of 3-methyl-6-acetoxymethyl-2,2'-bipyridine 1'-oxide are dissolved in 20 ml of benzene at 45° C., and 1.43 g (10.4 mmols) of phosphorus trichloride are added dropwise under an atmosphere of nitrogen. Subsequently, the mixture is boiled under reflux for 30 minutes. After cooling to 23° C., 35 ml of water are added and the benzene phase is separated off. The water phase is washed with twice 15 ml of ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated in vacuo. After distillation in a bulb tube oven at 125° C./0.13 Pa, 1.51 g (77% of theory) of 3-methyl-6-acetoxymethyl-2,2'-bipyridine are obtained in the form of a colourless oil.

Workup

  1. temperatureunder reflux for 30 minutes
  2. customthe benzene phase is separated off
  3. washThe water phase is washed with twice 15 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. distillationAfter distillation in a bulb tube oven at 125° C./0.13 Pa, 1.51 g (77% of theory) of 3-methyl-6-acetoxymethyl-2,2'-bipyridine
  7. customare obtained in the form of a colourless oil

Sources & evidence

ORD record
ord-3702a5d3242d4607ad986f756eb61fb3
Source dataset
uspto-grants-1984_01
Patent number
US04424359

Reaction notes

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