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

HRID 649177ノート

反応式

HRID 649177 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2b2a94c0358345aa875a3f8005d836f8
出典データセット
uspto-grants-1988_04
特許番号
US04738970

反応ノート

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