Water → HCID 67391087, compound

HRID 910772Notes

Reaction equation

HRID 910772 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:17]3[CH2:16][CH2:15][CH2:14][CH:13]([OH:18])[C:12]=3[C:11](=[O:19])[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:9]2)=[CH:3][CH:2]=1.[H-].[Na+].[CH3:33]I.O>CN(C)C=O>[C:1]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[C:17]3[CH2:16][CH2:15][CH2:14][CH:13]([O:18][CH3:33])[C:12]=3[C:11](=[O:19])[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:9]2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59627849HCID 59627849, compound

Product 1

HCID 67391087HCID 67391087, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Racemic ethyl 1-(biphenyl-4-ylmethyl)-5-hydroxy-4-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (Example 17, 174 mg, 0.431 mmol) was dissolved in degassed N,N-dimethylformamide (2 mL), cooled to 0° C. under an atmosphere of nitrogen and treated with sodium hydride (19 mg, 0.47 mmol, 60% dispersion in mineral oil, 1.1 equiv) and then methyl iodide (0.096 mL, 1.55 mmol, 3.6 equiv). After stirring for 15 min, the mixture was warmed to ambient temperature and stirred for an additional 1 hr. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined ethyl acetate extracts were washed once with water and brine, dried with sodium sulfate, filtered and concentrated in vacuo to provide racemic ethyl 1-(biphenyl-4-ylmethyl)-5-methoxy-4-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate.

Workup

  1. temperaturethe mixture was warmed to ambient temperature
  2. stirringstirred for an additional 1 hr
  3. extractionextracted three times with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed once with water and brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3697b2d2648544d0835c71066729b0c6
Source dataset
uspto-grants-2011_09
Patent number
US08022215B2

Reaction notes

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