Sodium Bicarbonate → HCID 22678498, compound

HRID 1837776Notes

Reaction equation

HRID 1837776 reaction equation
[O:1]=[C:2]1[C:11]([CH:12]=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH2:14]1[O:22][C:21]2[C:16](=[C:17]([CH2:23][CH2:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[CH:18]=[CH:19][CH:20]=2)[O:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(O)(=O)C>[O:1]=[C:2]1[C:11]([CH2:12][N:28]2[CH2:29][CH2:30][CH:25]([CH2:24][CH2:23][C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[O:22][CH2:14][O:15][C:16]=34)[CH2:26][CH2:27]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5893342-Hydroxyquinoline-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22678447HCID 22678447, compound

Product 1

HCID 22678498HCID 22678498, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of tetrahydrofuran were dissolved 0.24 g of 2-oxo-1,2-dihydro-3-quinolinecarboxaldehyde and 0.3 g of 4-[2-[2,3-(methylenedioxy)phenyl]ethyl]piperidine. To the mixture were added 0.5 ml of acetic acid and 0.42 g of sodium triacetoxyborohydride were added thereto, followed by stirring at room temperature for 12 hours. An aqueous saturated sodium bicarbonate aqueous solution was added to the reaction solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting solid was collected by filtration, to give 130 mg of the title compound as a light brown solid.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-ef927353ead248e29ab84e3af6eb8d3d
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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