Potassium Carbonate → HCID 67391613, compound

HRID 910770Notes

Reaction equation

HRID 910770 reaction equation
[O:1]=[C:2]1[C:11]2[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:6]=2[NH:5][CH:4]=[C:3]1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:5]2[C:6]3[CH2:7][CH2:8][CH2:9][C:10](=[O:12])[C:11]=3[C:2](=[O:1])[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 12876362Ethyl 4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Product 1

HCID 67391613HCID 67391613, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (1.56 g, 6.63 mmol) was dissolved in 20 mL of degassed N,N-dimethylformamide and treated with 4-bromobenzylbromide (1.99 g, 7.96 mmol) and potassium carbonate (1.10 g, 7.96 mmol). The mixture was stirred at ambient temperature for 18 hrs, and then partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate and the combined ethyl acetate extracts were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide ethyl 1-(4-bromobenzyl)-4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate.

Workup

  1. custompartitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washthe combined ethyl acetate extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aff630dcae674066954aa887b8e705ab
Source dataset
uspto-grants-2011_09
Patent number
US08022215B2

Reaction notes

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