Ethanol → Ethyl 3-methylpyridine-2-carboxylate

HRID 1410782노트

반응식

HRID 1410782 반응식
[CH3:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:15][CH2:16]O>>[CH2:15]([O:9][C:8]([C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10])[CH3:16]

참가 물질

4

반응물 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 2687573-Methylpicolinic acid

생성물 1

HCID 12243768Ethyl 3-methylpyridine-2-carboxylate

반응 조건

온도
-20 °C

실험 절차

3-Methyl-pyridine-2-carboxylic acid (1 g, 7.29 mmol) was dissolved in EtOH (50 mL) and cooled to −20° C. Thionyl chloride (1.1 mL, 14.6 mmol) was added, and the resulting white suspension was refluxed for 5 h, then concentrated to dryness. Water (10 mL) was added and solid Na2CO3 was added to neutralize the solution. The resulting mixture was extracted with ether. The organic layer was dried over MgSO4, and the solvent was removed by distillation to give 1.25 g of the title compound as an oil. 1H NMR (CDCl3, 200 MHz): δ=8.54 (d, 1H, J=3.9 Hz), 7.59 (d, 1H, J=7.8 Hz), 7.26-7.40 (m, 1H), 4.45 (q, 2H, J=7.0 Hz), 2.59 (s, 3H), 1.45 (t, 3H, J=7.0 Hz).

후처리

  1. temperaturethe resulting white suspension was refluxed for 5 h
  2. concentrationconcentrated to dryness
  3. additionWater (10 mL) was added
  4. additionsolid Na2CO3 was added
  5. extractionThe resulting mixture was extracted with ether
  6. dry with materialThe organic layer was dried over MgSO4
  7. customthe solvent was removed by distillation

출처 및 근거

ORD 기록
ord-373a833ed31247cbba6c2ec6e800dbad
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921389B2

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