Dimethylformamide → methyl 4-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)methyl]-3-[(methylsulfonyl)oxy]benzoate

HRID 507991

反応式

HRID 507991 の反応式
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][S:14]([CH3:17])(=[O:16])=[O:15].[CH3:18][CH:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[CH3:18][CH:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]1[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][S:14]([CH3:17])(=[O:16])=[O:15]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 962892-Methyl-1,2,3,4-tetrahydroquinolineHCID 23157330Methyl 4-(bromomethyl)-3-[(methylsulfonyl)oxy]benzoate

生成物 1

HCID 23157488methyl 4-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)methyl]-3-[(methylsulfonyl)oxy]benzoate収率 75%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

A mixture of methyl 4-(bromomethyl)-3-[(methylsulfonyl)oxy]benzoate (0.70 g, 2.2 mmol), 2-methyl-1,2,3,4-tetrahydroquinoline (0.39 g, 2.6 mmol), potassium carbonate (0.60 g, 4.3 mmol) and N,N-dimethylformamide (14 mL) was stirred at 70° C. for 23 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1) to give the title compound (0.63 g, yield 75%) as a pale-yellow oil.

後処理

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1)

出典と根拠

ORDレコード
ord-6312856ef23848778fe07efbc22e69ae
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

関連ノート

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