Dichloromethane → cis-4-(Acetyl-phenylamino)-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl ester

HRID 1352488ノート

反応式

HRID 1352488 の反応式
[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:14]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][C@@H:12]1[CH3:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH:35]([CH3:37])C)CC)(C)C.ClCCl.C(=O)([O-])[O-:42].[K+].[K+]>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:14]([N:21]([C:35](=[O:42])[CH3:37])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][C@@H:12]1[CH3:28])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 12093188cis-2-Methyl-4-phenylamino-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl ester

生成物 1

HCID 12093189cis-4-(Acetyl-phenylamino)-2-methyl-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl ester収率 64%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of cis-2-methyl-4-phenylamino-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (5.3 g), diisopropyl ethyl amine (2.73 g) in dioxane (31 ml), anhydride acetic (7.26 g) was added under stirring. The mixture was heated under reflux over night. After cooling, dichloromethane and an aqueous solution of potassium carbonate were added. The organic layer was separated, and then dried over sodium sulfate. Organic solvent was removed under reduce pressure to give the crude compound (18 g). The desired compound (3.8 g, 64% yield) was obtained after purification by flash chromatography on silica gel with cyclohexane/ethyl acetate (80/20) as eluent and then cyclohexane/ethyl acetate (50/50).

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux over night
  3. temperatureAfter cooling
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customOrganic solvent was removed
  7. customto give the crude compound (18 g)

出典と根拠

ORDレコード
ord-4072c7e77be0403e82a36a5059fec4ae
出典データセット
uspto-grants-2007_05
特許番号
US07220760B2

反応ノート

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