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

HRID 364996ノート

反応式

HRID 364996 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 132925992-(Hydroxymethyl)pyridine-4-carbonitrile収率 46%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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°.

後処理

  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)

出典と根拠

ORDレコード
ord-e2c246a9ddd0465cb224eed3b1b2f123
出典データセット
uspto-grants-1986_08
特許番号
US04607107

反応ノート

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