Methanol → 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylic acid

HRID 47458

反応式

HRID 47458 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].[N-:11]=[N+:12]=[N-:13].[Na+].CO.[C:17](OC(=O)C)(=O)[CH3:18]>>[CH3:17][C:18]1[N:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C:8]([OH:10])=[O:9])[N:13]=[N:12][N:11]=1

参加物

5

反応物 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 33557Sodium AzideHCID 4595313-Aminoisonicotinic acid

生成物 1

HCID 221726643-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylic acid

実験手順

3-Aminopyridine-4-carboxylic acid (50.0 g, 0.36 mol) was suspended in acetic anhydride (250 mL) then heated at reflux for 2 hours. The reaction mixture was concentrated under vacuum. The solid residue was slurried with heptane then concentrated under vacuum. The resulting solid was covered with acetic acid (300 mL), then sodium azide (23.5 g, 0.36 mol) was added. The reaction exothermed to 50° C. The reaction mixture was allowed to stir at ambient temperature overnight. The precipitate was isolated by filtration then slurried with methanol and filtered. The solid was dissolved in 10% sodium hydroxide. The solution was heated on a steam bath for 30 minutes, allowed to cool to ambient temperature then neutralized with 6N hydrochloric acid. The resulting precipitate was isolated by filtration, washed with water and dried to provide 64.5 g of 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylic acid as an off white solid, m.p. 214-215° C. (decomposition).

後処理

  1. temperaturethen heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. concentrationthen concentrated under vacuum
  5. customexothermed to 50° C
  6. customThe precipitate was isolated by filtration
  7. filtrationfiltered
  8. dissolutionThe solid was dissolved in 10% sodium hydroxide
  9. temperatureThe solution was heated on a steam bath for 30 minutes
  10. temperatureto cool to ambient temperature
  11. customThe resulting precipitate was isolated by filtration
  12. washwashed with water
  13. customdried

出典と根拠

ORDレコード
ord-7a113dd9843c441590b768d08b556382
出典データセット
uspto-grants-2004_03
特許番号
US06699878B2

関連ノート

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