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Water → 5-Hydroxypyridine-3-carbonitrile

HRID 1720920
ノート
印刷プレビュー

反応式

HRID 1720920 の反応式
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:9])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>N1C=CC=CC=1>[C:7]([C:6]1[CH:5]=[N:4][CH:3]=[C:2]([OH:1])[CH:10]=1)#[N:9]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 3543133-Pyridinecarboxamide, 5-hydroxy-

生成物 1

HCID 153421425-Hydroxypyridine-3-carbonitrile収率 70%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

5-Hydroxynicotinamide (0.69 g, 5 mmol) prepared by the method described in International Patent Publication No. 8606628 was dissolved in pyridine (50 ml). Trifluoroacetic anhydride (2.52 g, 12 mmol) was added, and the mixture was stirred at 0° C. for 20 hours. The reaction mixture, to which water (20 ml) was added, was concentrated under reduced pressure and extracted with chloroform (50 ml×3). The chloroform layer was washed with water (50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (Wako Gel C-200, 20 g; eluted with chloroform:methanol=100:1) to give 3-cyano-5-hydroxypyridine (0.42 g, 3.5 mmol) (Yield 70%).

後処理

  1. concentrationwas concentrated under reduced pressure
  2. extractionextracted with chloroform (50 ml×3)
  3. washThe chloroform layer was washed with water (50 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue
  7. customThe residue was purified by silica gel column chromatography (Wako Gel C-200, 20 g; eluted with chloroform:methanol=100:1)

出典と根拠

ORDレコード
ord-b3969444477b436c82510515b1255be8
出典データセット
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05508293

反応ノート

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