Lithium Hydroxide → HCID 69427262, compound

HRID 1352497Notes

Reaction equation

HRID 1352497 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]([N:7]([C@H:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:16]([CH3:32])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[OH-].[Li+].ClCCl.C(=O)(O)[O-].[Na+]>CO.O>[C:24]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5](=[O:6])[CH2:4][C:3]([OH:33])=[O:2])[CH2:15][C@@H:16]1[CH3:32])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 3939Lithium Hydroxide2×HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 69427617HCID 69427617, compound

Product 1

HCID 69427262HCID 69427262, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of Cis-N-(1-Benzoyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-phenyl-malonamic acid methyl ester (0.031 g) in a mixture of methanol (1 ml) and water (1 ml), 0.0067 g of lithium hydroxide was added under stirring at room temperature, over night. In order to complete the reaction, 0.0067 g of lithium hydroxide was added and the mixture was stirred over night. Then dichloromethane and an aqueous solution of sodium bicarbonate were added, the organic layer was separated, dried over sodium sulfate, the solvent was removed under reduce pressure to give a solid which was purified by flash chromatography with dichloromethane/methanol (95/5) as eluent to give a solid (0.01 g, 33.3% yield).

Workup

  1. additionwas added
  2. additionwas added
  3. stirringthe mixture was stirred over night
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed
  7. customto give a solid which
  8. customwas purified by flash chromatography with dichloromethane/methanol (95/5) as eluent

Sources & evidence

ORD record
ord-6c43b3adaf324a35a58b349df893d4fc
Source dataset
uspto-grants-2007_05
Patent number
US07220760B2

Reaction notes

Loading…