Methylamine → 3-hydroxy-N-methylbenzamide

HRID 491630

反応式

HRID 491630 の反応式
[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]

参加物

6

反応物 4

HCID 6329MethylamineHCID 74203-Hydroxybenzoic AcidHCID 8028TetrahydrofuranHCID 24386Thionyl Chloride

生成物 1

HCID 3537103-hydroxy-N-methylbenzamide

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. customThe solvent was removed
  4. dissolutionthe crude was dissolved in anhydrous THF (100 mL)
  5. customwas formed
  6. customThe solvent was evaporated
  7. dissolutionthe residue was dissolved in MTBE
  8. washwashed with sat. NH4Cl (aq.)
  9. dry with materialThe organic layer was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customFurther purification by column chromatography (0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-660ac45de33249469209d51bd48be8cd
出典データセット
uspto-grants-2009_05
特許番号
US07531553B2

関連ノート

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