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

HRID 507991

반응식

HRID 507991 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6312856ef23848778fe07efbc22e69ae
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

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