Hydrochloric Acid → 1-(Quinolin-6-yl)ethan-1-one

HRID 40325

反応式

HRID 40325 の反応式
CON(C)[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)=[O:5].[CH2:17]1COCC1.C[Mg]Br.Cl>>[N:12]1[C:13]2[C:8](=[CH:7][C:6]([C:4](=[O:5])[CH3:17])=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 55211172N-Methoxy-N-methylquinoline-6-carboxamideHCID 178418573HCID 178418573、化合物HCID 178418689HCID 178418689、化合物

生成物 1

HCID 2585591-(Quinolin-6-yl)ethan-1-one収率 86.6%

実験手順

A 250 mL RB flask was charged with N-methoxy-N-methylquinoline-6-carboxamide (5.943 g, 27.5 mmol) and THF (100 ml, 1220 mmol), then cooled to 0 C. Methylmagnesium bromide (18.3 ml, 55.0 mmol) was added dropwise and the mixture was allowed to warm to room temperature and stirred for 3 hours. The reaction was not quite complete, so additional MeMgBr (3 mL) was added and the mixture was stirred overnight. The mixture was then neutralized using 2N HCl and the aqueous layer was extracted with DCM (200 mL×2) and EtOAc (200 mL×2). The organic layer was dried with MgSO4, filtered, and concentrated to give a yellow oil. The aqueous layer contained some product, so the layer was concentrated and then filtered thru a reverse phase C18 column, first eluting with water than with MeOH. The MeOH layer was concentrated to give a yellow oil which was combined with the yellow oil from the organic layer. The combined portions were purified by MPLC eluting with a gradient of 2-6% MeOH/DCM. 1-(quinolin-6-yl)ethanone (4.074 g, 86.6% yield) was isolated as a yellow oil which solidified upon standing.

後処理

  1. temperaturecooled to 0 C
  2. stirringthe mixture was stirred overnight
  3. extractionthe aqueous layer was extracted with DCM (200 mL×2) and EtOAc (200 mL×2)
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow oil
  8. concentrationso the layer was concentrated
  9. filtrationfiltered
  10. washfirst eluting with water than with MeOH
  11. concentrationThe MeOH layer was concentrated
  12. customto give a yellow oil which
  13. customThe combined portions were purified by MPLC
  14. washeluting with a gradient of 2-6% MeOH/DCM

出典と根拠

ORDレコード
ord-c318b55a1f8847c9a3f0ed6886452e4f
出典データセット
uspto-grants-2013_09
特許番号
US08524900B2

関連ノート

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