Sulfuric Acid → 5-Hydroxypyridine-2-carbonitrile

HRID 406516

반응식

HRID 406516 반응식
S(=O)(=O)(O)O.N[C:7]1[CH:8]=[N:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=1.N([O-])=[O:16].[Na+]>O.C(OCC)(=O)C>[OH:16][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[N:9][CH:8]=1

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 38713955-Aminopyridine-2-carbonitrileHCID 23668193Sodium Nitrite

생성물 1

HCID 214137735-Hydroxypyridine-2-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

Concentrated sulfuric acid (21.0 mL) was added to a suspension of 3-amino-6-cyanopyridine (5.00 g, 42.0 mmol) in water (75.0 mL), and then a 1.6 M aqueous solution of sodium nitrite (29.0 mL, 46.4 mmol) was slowly added dropwise thereto under ice water cooling. This suspension was stirred for 6 hours at 100° C. The reaction mixture was cooled to room temperature, and then was diluted with ethyl acetate (100 mL). The organic layer was washed sequentially with water and saturated brine, and was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1, v/v). Thus, the title compound was obtained.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane

출처 및 근거

ORD 기록
ord-1d7052acebb94fe69e24479fd6e409ca
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754112B2

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