Water → cis-2-Methyl-4-phenylamino-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl ester

HRID 1352487ノート

反応式

HRID 1352487 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:14](=[N:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][CH:12]1[CH3:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C1CCCCC1>[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 2

HCID 962WaterHCID 120931872-Methyl-4-phenylimino-3,4-dihydro-2H-quinoline-1-carboxylic Acid Benzyl Ester

生成物 1

HCID 12093188cis-2-Methyl-4-phenylamino-3,4-dihydro-2h-quinoline-1-carboxylic acid benzyl ester収率 46.6%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 8078Cyclohexane溶媒HCID 5049666Sodium triacetoxyborohydride溶媒

実験手順

To a solution of 2-methyl-4-phenylimino-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester (16 g) in acetic acid (450 ml), sodium triacetoxyborohydride was added in small amounts (32.32 g), under stirring, at room temperature. The reaction mixture was then stirred at room temperature for one hour and poured on 1 liter of cold water under stirring. After precipitation, the mixture was filtered, dissolved in ethyl acetate and then, washed with water. The organic layer was separated and dried over sodium sulfate. The solvent was removed to give the crude compound (9g), recristallised in hot cyclohexane (40 ml), and then filtered at room temperature to give the desired compound (5.3 g, 46.6% yield).

後処理

  1. stirringThe reaction mixture was then stirred at room temperature for one hour
  2. stirringunder stirring
  3. customAfter precipitation
  4. filtrationthe mixture was filtered
  5. dissolutiondissolved in ethyl acetate
  6. washwashed with water
  7. customThe organic layer was separated
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed
  10. customto give the crude compound (9g)
  11. filtrationfiltered at room temperature

出典と根拠

ORDレコード
ord-1443954de1d64102a48a3d0065f448be
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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