Ethyl chloroformate → HCID 19039847, compound

HRID 1684539Notes

Reaction equation

HRID 1684539 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]([C:13]([O:15][CH3:16])=[O:14])[CH2:7][CH2:6]2.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:8]([C:13]([O:15][CH3:16])=[O:14])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 21950627Methyl 6-methoxy-1,2,3,4-tetrahydroquinoline-2-carboxylate

Product 1

HCID 19039847HCID 19039847, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 69.3 g (0,313 mol) of (±)-6-methoxy-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline and 39 ml (0.407 mol) of ethyl chloroformate in 1400 ml of dichloromethane are added 85 g (0.63 mol) of potassium carbonate, and the mixture is heated at reflux for 18 h. The mixture is filtered, the filtrate is concentrated under reduced pressure and the residue is chromatographed on a column of silica, with a 3/7 mixture of ethyl acetate and cyclohexane. 80.4 g of product are obtained in the form of an oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 18 h
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customthe residue is chromatographed on a column of silica, with a 3/7 mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-7a1e7ecc148b4b0a8a7bbe025a087781
Source dataset
uspto-grants-1997_06
Patent number
US05641785

Reaction notes

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