Methanol → 6-(2-Oxoethyl)nicotinonitrile

HRID 1466046Notes

Reaction equation

HRID 1466046 reaction equation
[CH2:1]([C:4]1[N:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1)[CH:2]=C.C[OH:13]>C(Cl)Cl>[O:13]=[CH:2][CH2:1][C:4]1[N:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 107968686-Allylnicotinonitrile

Product 1

HCID 895250136-(2-Oxoethyl)nicotinonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

A mixture of 6-(Prop-2-en-1-yl)pyridine-3-carbonitrile (4.8 g, 33 mmol) in 80 mL of DCM and 20 mL of MeOH was cooled to −70° C. Ozone was bubbled through the mixture until the mixture turned blue (about 20 minutes). The excess of ozone was removed by flush with N2 flow until the mixture turned colorless. 5 mL of Me2S was added to the mixture which was then warmed slowly to room temperature and stirred for 2 hours. The solvent was removed under vacuum below 30° C. to afford the title compound which was used without further purification.

Workup

  1. customOzone was bubbled through the mixture until the mixture
  2. custom(about 20 minutes)
  3. customThe excess of ozone was removed
  4. customby flush with N2 flow until the mixture
  5. addition5 mL of Me2S was added to the mixture which
  6. temperaturewas then warmed slowly to room temperature
  7. customThe solvent was removed under vacuum below 30° C.

Sources & evidence

ORD record
ord-9a02be7ad62f409aa48c5221d2671734
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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