Hydrochloric Acid → 6-bromo-2-methoxycarbonylmethyl-N-ethoxalyltetrahydroquinoline

HRID 862563Notes

Reaction equation

HRID 862563 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]2.C(N(CC)CC)C.[C:24](Cl)(=[O:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26].Cl>ClCCl>[Br:1][C:2]1[CH2:3][CH:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:30])[CH:7]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 104016006-Bromo-2-methoxycarbonylmethyltetrahydroquinoline

Product 1

HCID 676514876-bromo-2-methoxycarbonylmethyl-N-ethoxalyltetrahydroquinolineYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-bromo-2-methoxycarbonylmethyltetrahydroquinoline (43.8 g, 0.153 mol) and triethylamine (37.5 g, 0.371 mol) in dichloromethane (700 mL) was added slowly ethyl chlorooxalate (25.5 g, 0.187 mol) at 0° C. The mixture was stirred for 3 h at 0° C., poured into 0.3N hydrochloric acid (750 mL) and extracted with dichloromethane. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 4:1 to 3:1 hexane/ethyl acetate to give 56.9 g of the title compound (97%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 4:1 to 3:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-bb961224de074b6582ba235146f50589
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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