Sulfuric Acid → 5-Hydroxypyridine-2-carbonitrile

HRID 406516

反応式

HRID 406516 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 214137735-Hydroxypyridine-2-carbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1d7052acebb94fe69e24479fd6e409ca
出典データセット
uspto-grants-2014_06
特許番号
US08754112B2

関連ノート

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