Water → HCID 22935713, compound

HRID 1352494Notes

Reaction equation

HRID 1352494 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10](=[N:12][CH2:13][C:14]#[CH:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].O>C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[CH3:1][CH:2]1[CH2:11][CH:10]([NH:12][CH2:13][C:14]#[CH:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]

Participants

5

Reactant 2

HCID 962WaterHCID 22935746HCID 22935746, compound

Product 1

HCID 22935713HCID 22935713, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 5049666Sodium triacetoxyborohydrideSolvent

Procedure

To a solution of (2-methyl-4-prop-2-ynylimino-3,4-dihydro-2H-quinolin-1-yl)-phenyl-methanone (0.5 g) in acetic acid (20 ml), sodium triacetoxyborohydride was added in small amounts (1.75 g) under stirring at room temperature. The reaction mixture was then stirred at room temperature for one hour and poured on 100 ml of cold water under stirring. The desired compound was filtered after precipitation. The compound was dissolved in ethyl acetate and washed with water. The organic layer was separated and dried over sodium sulfate. The solvent was removed under reduce pressure to give a brown oil which was purified by flash chromatography with cyclohexane/ethyl acetate (95/5) as eluent and then cyclohexane/ethyl acetate (90/10) to give a mixture of diastereoisomere cis-trans (50–50) of (2-methyl-4-prop-2-ynylamino-3,4-dihydro-2H-quinolin-1-yl)-phenyl-methanone (0.06 g, 17.6% yield).

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for one hour
  2. stirringunder stirring
  3. filtrationThe desired compound was filtered
  4. customafter precipitation
  5. dissolutionThe compound was dissolved 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 a brown oil which
  11. customwas purified by flash chromatography with cyclohexane/ethyl acetate (95/5) as eluent
  12. customcyclohexane/ethyl acetate (90/10) to give

Sources & evidence

ORD record
ord-6a9ab8d930a44614a25a459cd3846235
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

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