Triethylamine → Ethyl 7-bromo-2,4-dioxo-1-(propan-2-yl)-1,2,3,4-tetrahydroquinoline-3-carboxylate

HRID 1754558Notes

Reaction equation

HRID 1754558 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([N:11]([C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]([CH3:14])[CH3:13])[CH:3]=1.C(N(CC)CC)C.S(Cl)(Cl)=O>ClCCCl.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:8])[CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:15](=[O:22])[N:11]2[CH:12]([CH3:14])[CH3:13])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 866798024-Bromo-2-[(3-ethoxy-3-oxopropanoyl)(propan-2-yl)amino]benzoic acid

Product 1

HCID 86679803Ethyl 7-bromo-2,4-dioxo-1-(propan-2-yl)-1,2,3,4-tetrahydroquinoline-3-carboxylateYield 52%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-[(3-ethoxy-3-oxopropanoyl)(propan-2-yl)amino]benzoic acid (6.2 g, 16.7 mmol) in 170 mL of DCE is added triethylamine (3.5 mL, 25.1 mmol), followed by addition of thionyl chloride (1.45 mL, 20.6 mmol) at 0° C. After stirring at room temperature for 3 hours, the reaction medium is diluted with DCM and washed with aqueous HCl solution (1M). The organic phase is washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution, dried over Na2SO4 and concentrated to dryness. The oil obtained is purified by flash chromatography (toluene/EtOAc: 100/0 to 90/10) to give 2,23 g of a white solid (yield: 52%).

Workup

  1. washwashed with aqueous HCl solution (1M)
  2. washThe organic phase is washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe oil obtained
  6. customis purified by flash chromatography (toluene/EtOAc: 100/0 to 90/10)

Sources & evidence

ORD record
ord-b3d0c380de034b58982055249842d518
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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