Methanol → Methyl 2-methylisonicotinate

HRID 479767

반응식

HRID 479767 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:15]O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([O:7][CH3:15])=[O:6]

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27628212-Methylpyridine-4-carboxylic acid

생성물 1

HCID 11542811Methyl 2-methylisonicotinate수율 61%

실험 절차

To an ice-cooled suspension of 1.32 g (9.62 mmol) of 2-methylisonicotinic acid in 20 mL of MeOH was added 1.47 mL (20.2 mmol) of thionyl chloride. The ice-bath was removed and the reaction was stirred at rt. After 22 h, the MeOH was evaporated and the residue was taken up in H2O. The aqueous mixture was neutralized with saturated NaHCO3, then extracted with Et2O. The organic extracts were washed with saturated NaCl, dried over MgSO4, then filtered through a bed of celite. Eva-poration of solvent in vacuo afforded the title compound as a yellow liquid (0.89 g, 61%): 1H NMR (CDCl3): d 8.66 (d, 1H); 7.72 (s, 1H); 7.64 (d, 1H); 3.98 (s, 3H); 2.64 (s, 3H).

후처리

  1. customThe ice-bath was removed
  2. customthe MeOH was evaporated
  3. extractionextracted with Et2O
  4. washThe organic extracts were washed with saturated NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered through a bed of celite

출처 및 근거

ORD 기록
ord-1f78b6aefe504983ae943362f6cec512
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645989B2

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