Water → HCID 21445368, compound

HRID 1414313Notes

Reaction equation

HRID 1414313 reaction equation
[CH2:1]([CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1)[CH3:2].C([O:15][CH:16]=[C:17]([C:23](OCC)=O)[C:18]([O:20]CC)=[O:19])C.O>[OH-].[Na+]>[CH2:1]([CH:3]1[N:4]2[C:5]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[CH2:11][CH2:12]1)[C:16](=[O:15])[C:17]([C:18]([OH:20])=[O:19])=[CH:23]2)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 14299241HCID 14299241, compound

Product 1

HCID 21445368HCID 21445368, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
127.5 °C

Procedure

Following the procedure set forth in Example 1, 2-ethyltetrahydroquinoline is mixed with diethyl ethoxymethylenemalonate and heated to 125 to 130° C. for 2 hours. Polyphosphoric acid is added, and the mixture is heated at 115° C. for one hour. The mixture is poured into water, neutralized with 40 percent sodium hydroxide, and the product is isolated and saponified in 10 percent sodium hydroxide solution. The solution is neutralized, and the solid product, 6,7-dihydro-5-ethyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, is isolated by filtration.

Workup

  1. temperaturethe mixture is heated at 115° C. for one hour
  2. customthe product is isolated

Sources & evidence

ORD record
ord-883bc199a7c24904a35adcc822846347
Source dataset
uspto-grants-1977_01
Patent number
US04001243

Reaction notes

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