Water → HCID 58307003, compound

HRID 1909849Notes

Reaction equation

HRID 1909849 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].BrC[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.O>CN(C=O)C.C(OCC)(=O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][C:9]=3[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:3][CH2:2]2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 230291-(2-Bromoethyl)-4-chlorobenzeneHCID 24758Sodium hydride2×HCID 13951737Ethyl 1,2,3,4-tetrahydro-8-quinolinecarboxylate

Product 1

HCID 58307003HCID 58307003, compoundYield 28.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl 1,2,3,4-tetrahydroquinoline-8-carboxylate (1.1 g) and DMF (9.0 mL) was added sodium hydride (55% dispersion in paraffin liquid, 280 mg) at 0° C., followed by stirring at room temperature for 30 minutes. To the reaction mixture was added a solution of 1-(bromoethyl)-4-chlorobenzene (1.2 g) in DMF (2.0 mL) under ice-cooling, followed by stirring at room temperature for 3 days. To the reaction mixture was added sodium hydride (55% dispersion in paraffin liquid, 280 mg), followed by stirring for 1 day. To the reaction mixture were added water and ethyl acetate, and a liquid-separation operation was carried out. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain ethyl 1-(4-chlorobenzyl)-1,2,3,4-tetrahydroquinoline-8-carboxylate (510 mg).

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 3 days
  3. stirringby stirring for 1 day
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-3a909b71a8df457a80c4c3348f680c25
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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