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

HRID 1422074노트

반응식

HRID 1422074 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 42999103-Hydroxy-6-n-propylpyridine

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f8a9327ff9924cd7b4ce6b2894b420f3
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06080754

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