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

HRID 1352487Notes

Reaction equation

HRID 1352487 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8078CyclohexaneSolventHCID 5049666Sodium triacetoxyborohydrideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1443954de1d64102a48a3d0065f448be
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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