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Water → 5-Hydroxypyridine-3-carbonitrile

HRID 1720920
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HRID 1720920 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

HCID 153421425-Hydroxypyridine-3-carbonitrile수율 70%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-b3969444477b436c82510515b1255be8
출처 데이터셋
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05508293

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