Water → 3-Amino-4,6-dibromopyridine-2-carboxylic acid

HRID 887730ノート

反応式

HRID 887730 の反応式
[NH2:1][C:2]1[C:3](C#N)=[N:4][C:5]([Br:9])=[CH:6][C:7]=1[Br:8].O.[C:13](=[O:16])(O)[O-:14].[Na+]>S(=O)(=O)(O)O>[NH2:1][C:2]1[C:3]([C:13]([OH:14])=[O:16])=[N:4][C:5]([Br:9])=[CH:6][C:7]=1[Br:8]

参加物

5

反応物 3

HCID 962Water2 回HCID 516892Sodium BicarbonateHCID 593552783-Amino-4,6-dibromo-2-pyridinecarbonitrile

生成物 1

HCID 529112383-Amino-4,6-dibromopyridine-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
100 °C

実験手順

3-amino-4,6-dibromo-pyridine-2-carbonitrile (158 mg) was dissolved in concentrated sulfuric acid (1.5 mL) and stirred for 1 h at 100° C. The reaction mixture was cooled to room temperature and water (1.5 mL) was slowly added. The reaction mixture was warmed again to 100° C. and stirred at this temperature for 2 h. Water was added after cooling to room temperature, the pH was adjusted to −10 by addition of solid sodium bicarbonate and the aqueous solution was washed 2× with MTB-ether. The aqueous layer was then adjusted to pH ˜2 by addition of 2 M hydrochloric acid and extracted 3× with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuum to afford 123 mg of the title compound of the formula

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureThe reaction mixture was warmed again to 100° C.
  3. stirringstirred at this temperature for 2 h
  4. temperatureafter cooling to room temperature
  5. washthe aqueous solution was washed 2× with MTB-ether
  6. additionThe aqueous layer was then adjusted to pH ˜2 by addition of 2 M hydrochloric acid
  7. extractionextracted 3× with ethyl acetate
  8. washThe combined organic layer was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-6b9e3cc8c1b24bc88f487b3a828e0966
出典データセット
uspto-grants-2012_08
特許番号
US08247431B2

反応ノート

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