Sodium Bicarbonate → 3-Hydroxy-6-n-propylpyridine

HRID 1422074ノート

反応式

HRID 1422074 の反応式
N[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH3:10])=[N:6][CH:7]=1.N([O-])=[O:12].[Na+].C(=O)([O-])O.[Na+]>Cl.O>[OH:12][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH3:10])=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 138607306-Propylpyridin-3-amineHCID 23668193Sodium Nitrite

生成物 1

HCID 42999103-Hydroxy-6-n-propylpyridine

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

5-Amino-2-n-propylpyridine (70.3 g, 516 mmol) was dissolved in 1300 ml of 1M hydrochloric acid and sodium nitrite (35.6 g, 516 mmol) dissolved in 300 ml of water was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1/2 hour, heated to 70° C. for 2 hours, and then stirred at room temperature the overnight. The reaction mixture was neutralised to pH=8 by adding solid sodium hydrogen carbonate, and the product was extracted into ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and the solvent was evaporated. The crude product was purified by column chromatography over silica gel 60, using ethyl acetate:petroleum ether (1:1) as the eluent. This gave 65.7 g (92%) of 5-hydroxy-2-n-propylpyridine as an orange wax. 1H-NMR (CDCl3, 200 MHz) δ: 0.91 (t, 3H); 1.68 (sext, 2H); 2.71 (t, 2H); 7.09 (d, 1H); 7.25 (dd, 1H); 8.13 (d, 1H); 11.79 (s, 1H).

後処理

  1. additionwas added dropwise at 0° C
  2. temperatureheated to 70° C. for 2 hours
  3. stirringstirred at room temperature the overnight
  4. extractionthe product was extracted into ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated
  8. customThe crude product was purified by column chromatography over silica gel 60

出典と根拠

ORDレコード
ord-f8a9327ff9924cd7b4ce6b2894b420f3
出典データセット
uspto-grants-2000_06
特許番号
US06080754

反応ノート

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