Methanol → 2-(Hydroxymethyl)pyridine-4-carbonitrile

HRID 851484Notes

Reaction equation

HRID 851484 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)#[N:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[CH3:21][OH:22].S(=O)(=O)(O)O>O>[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:21][OH:22])[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 75064-CyanopyridineHCID 62648Ammonium Persulfate

Product 1

HCID 132925992-(Hydroxymethyl)pyridine-4-carbonitrileYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-cyanopyridine (31.2 g), ammonium persulphate (136.8 g), methanol (450 ml), concentrated sulphuric acid (16.2 ml) and water (210 ml) was heated under reflux for 24 hours, and the methanol was removed by distillation. Crushed ice (450 g) was added and the mixture was adjusted to pH 12 with 10 M sodium hydroxide and extracted with chloroform. The chloroform extracts were combined and evaporated and the residue was purified by elution from a silica gel column with methanol-chloroform (7.5% v/v) to give 4-cyano-2-hydroxymethylpyridine (18.5 g, 46%) m.p. 92°-94°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customthe methanol was removed by distillation
  4. additionCrushed ice (450 g) was added
  5. extractionextracted with chloroform
  6. customevaporated
  7. customthe residue was purified by elution from a silica gel column with methanol-chloroform (7.5% v/v)

Sources & evidence

ORD record
ord-6c9f9e3b11d54d24a0c4106ad68af9eb
Source dataset
uspto-grants-1983_05
Patent number
US04385058

Reaction notes

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