Diethyl (ethoxymethylene)malonate → HCID 13825638, compound

HRID 1702139Notes

Reaction equation

HRID 1702139 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH:9]([CH3:15])[NH:10]2)(=[O:3])[CH3:2].C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C>>[C:1]([NH:4][C:5]1[C:6]2=[C:11]3[N:10]([CH:9]([CH3:15])[CH2:8][CH2:7]2)[CH:26]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19](=[O:18])[C:12]3=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 13156215N-(2-Methyl-1,2,3,4-tetrahydroquinolin-5-yl)acetamide

Product 1

HCID 13825638HCID 13825638, compound

Conditions

Temperature
160 °C

Procedure

A mixture of 19 g of 5-acetamido-1,2,3,4-tetrahydroquinaldine and 24.0 g of diethyl ethoxymethylenemalonate was heated at 160° C. for 2 hours. The product obtained was not purified. To the mixture was added 60 g of polyphosphoric acid, and the mixture was heated at 100° C. for one hour. To the mixture was added 400 ml of warm water. The mixture was basified and cooled. The solid residue was separated by decantation to provide ethyl 8-acetamido-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate. Next the solid was dissolved in 20 ml of methanol, and to this solution was added 80 ml of ten percent sodium hydroxide solution. The solution was heated on a steam bath for one hour, followed by the addition of 20 ml of concentrated ammonium hydroxide. The solution was acidified to pH 6 with acetic acid. A solid precipitate formed which was separated by filtration and recrystallized from aqueous N,N-dimethylformamide to provide brown crystals of 8-amino-6,7-dihydro- 5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid. The structure was confirmed by infrared and nuclear magnetic resonance spectral analysis.

Workup

  1. customThe product obtained
  2. customwas not purified
  3. additionTo the mixture was added 60 g of polyphosphoric acid
  4. temperaturethe mixture was heated at 100° C. for one hour
  5. additionTo the mixture was added 400 ml of warm water
  6. temperaturecooled
  7. customThe solid residue was separated by decantation

Sources & evidence

ORD record
ord-90d5a89253174742aac6a94b37abc741
Source dataset
uspto-grants-1983_04
Patent number
US04380543

Reaction notes

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