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

HRID 1352487노트

반응식

HRID 1352487 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8078Cyclohexane용매HCID 5049666Sodium triacetoxyborohydride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1443954de1d64102a48a3d0065f448be
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220760B2

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