Racemic Ethyl 6,7-Dimethoxy-3-hydroxymethylene-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate → 3-Propargylaminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester

HRID 328808Notes

Reaction equation

HRID 328808 reaction equation
O[CH:2]=[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[N:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:4]1[CH3:23]>C1C=CC=CC=1>[CH2:4]([NH:5][CH:2]=[C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([O:14][CH3:15])[CH:10]=2)[N:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:4]1[CH3:23])[C:3]#[CH:2]

Participants

3

Reactant 1

HCID 70638946Racemic Ethyl 6,7-Dimethoxy-3-hydroxymethylene-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylate

Product 1

HCID 867338913-Propargylaminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 1.6 g. of 3-hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid, ethyl ester in 15 ml. of benzene is added 275 mg. of proparglyamine, and the resulting solution allowed to stir overnight at room temperature. The reaction mixture is concentrated in vacuo to about 2 g. and is then dissolved in 50 ml. of chloroform. The resulting solution is washed with 50 ml. of a 1N aqueous sodium hydroxide solution and subsequently dried over magnesium sulfate. Removal of the chloroform solvent leaves 1.9 g. of the desired product as a yellow foam.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo to about 2 g
  2. dissolutionand is then dissolved in 50 ml
  3. washThe resulting solution is washed with 50 ml
  4. dry with materialof a 1N aqueous sodium hydroxide solution and subsequently dried over magnesium sulfate
  5. customRemoval of the chloroform solvent
  6. customleaves 1.9 g

Sources & evidence

ORD record
ord-51ce068177fc4b93bb4bb38ec3759d44
Source dataset
uspto-grants-1977_04
Patent number
US04018758

Reaction notes

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