Water → HCID 72343106, compound

HRID 910769

Reaction equation

HRID 910769 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:13](=[O:17])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2].[Br:18][CH:19]=[CH:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:18][CH:19]=[CH:20][CH2:21][N:8]1[C:9]2[CH2:10][CH2:11][CH2:12][C:13](=[O:17])[C:14]=2[C:15](=[O:16])[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 52010281,3-DibromopropeneHCID 12876362Ethyl 4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Product 1

HCID 72343106HCID 72343106, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl-4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (714 mg, 3.04 mmol) was suspended in degassed N,N-dimethylformamide (8 mL) and treated with 1,3-dibromo-1-propene (0.364 mL, 3.64 mmol, 1.2 equiv) and potassium carbonate (503 mg, 3.64 mmol, 1.2 equiv). After stirring for 7 hrs at ambient temperature, the 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 afforded ethyl 1-[3-bromoprop-2-en-1-yl]-4,5-dioxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate as a mixture of E- and Z-isomers. Additional compound was obtained by concentration of the aqueous extract in vacuo and extraction of the resulting residue with a mixture of 80% chloroform and 20% methanol (v/v).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined ethyl acetate extracts were washed once with water and brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55a7999a8f44485ba64ad45c3368732a
Source dataset
uspto-grants-2011_09
Patent number
US08022215B2

Linked notes

Loading…