Sodium Carbonate → 8-Chloro-3-methyl-5,6,7,8-tetrahydroquinoline

HRID 649177노트

반응식

HRID 649177 반응식
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.CS([Cl:16])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([Cl:16])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 1200283-Methyl-5,6,7,8-tetrahydroquinoline

생성물 1

HCID 122789658-Chloro-3-methyl-5,6,7,8-tetrahydroquinoline수율 31.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 7.02 g of 3-methyl-5,6,7,8-tetrahydroquinoline was added dropwise 9.62 g of methanesulfonyl chloride under ice-cooled condition. The reaction mixture was stirred under ice-cooling condition for 2 hours, then further stirred at 80° C. for 3 hours. To the reaction mixture was added water, and this solution was made alkaline by adding sodium carbonate, then extracted with diethyl ether. The diethyl ether layer was washed with an aqueous solution saturated with sodium chloride, and dried with anhydrous magnesium sulfate. The solvent was removed by evaporation, then thus obtained residue was purified by a silica gel column chromatography (eluent: dichloromethane/methanol=100/1) to obtain 2.74 g of 3-methyl-8-chloro-5,6,7,8-tetrahydroquinoline.

후처리

  1. temperaturecooled condition
  2. temperaturecooling condition for 2 hours
  3. stirringfurther stirred at 80° C. for 3 hours
  4. extractionextracted with diethyl ether
  5. washThe diethyl ether layer was washed with an aqueous solution saturated with sodium chloride
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was removed by evaporation
  8. customthus obtained residue was purified by a silica gel column chromatography (eluent: dichloromethane/methanol=100/1)

출처 및 근거

ORD 기록
ord-2b2a94c0358345aa875a3f8005d836f8
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04738970

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