Methylamine → 3-hydroxy-N-methylbenzamide
반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].O=S(Cl)Cl.[CH3:15][NH2:16].C1COCC1>O1CCOCC1>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:16][CH3:15])=[O:6]참가 물질
6
실험 절차
To a solution of 3-hydroxybenzoic acid (10 g, 72 mmol, 1.0 eq.) in 100 mL of anhydrous dioxane was added SOCl2 (6.5 mL, 72 mmol, 1.0 eq.). The solution was heated to reflux and stirred for 4 h. The solvent was removed and the crude was dissolved in anhydrous THF (100 mL). A solution of 2 M CH3NH2 in THF (7.2 mL, 144 mmol, 2.0 eq.) was added upon which a white suspension was formed. The solvent was evaporated and the residue was dissolved in MTBE, washed with sat. NH4Cl (aq.). The organic layer was dried (MgSO4), filtered and concentrated. Further purification by column chromatography (0-100% EtOAc in hexanes) yielded 3-hydroxy-N-methyl-benzamide.
후처리
- temperatureThe solution was heated
- temperatureto reflux
- customThe solvent was removed
- dissolutionthe crude was dissolved in anhydrous THF (100 mL)
- customwas formed
- customThe solvent was evaporated
- dissolutionthe residue was dissolved in MTBE
- washwashed with sat. NH4Cl (aq.)
- dry with materialThe organic layer was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customFurther purification by column chromatography (0-100% EtOAc in hexanes)
출처 및 근거
- ORD 기록
- ord-660ac45de33249469209d51bd48be8cd
- 출처 데이터셋
- uspto-grants-2009_05
- 특허 번호
- US07531553B2
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