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

HRID 364996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 364996
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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 10M 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°.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e2c246a9ddd0465cb224eed3b1b2f123
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04607107

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