Ethanol → HCID 12911930, compound

HRID 2058496Notes

Reaction equation

HRID 2058496 reaction equation
C(O[CH:4]=[C:5]([C:11]([O-:13])=O)[C:6]([O:8]CC)=[O:7])C.[Cl:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH2:20][CH2:19][CH2:18]2.C(O)C.[OH-].[Na+]>O>[Cl:14][C:15]1[CH:24]=[C:23]2[C:22]3[N:21]([CH:4]=[C:5]([C:6]([OH:8])=[O:7])[C:11]2=[O:13])[CH2:20][CH2:19][CH2:18][C:17]=3[CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 111828396-Chloro-1,2,3,4-tetrahydroquinolineHCID 858292113-Ethoxy-2-ethoxycarbonylprop-2-enoate

Product 1

HCID 12911930HCID 12911930, compoundYield 111.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

4.9 g of ethyl ethoxymethylenemalonate was added to 4 g of 6-chloro-1,2,3,4-tetrahydroquinoline and the mixture was heated on an oil bath at 110° C. during which time distillation of ethanol was observed. After heating the mixture at the same temperature as above for 30 minutes, 30 g of polyphosphoric acid was added thereto followed by heating at 140° C. for 30 minutes. After completion of the reaction, the reaction mixture was poured into 200 ml of water and the resulting mixture was rendered neutral with a 40% aqueous sodium hydroxide solution to precipitate light brown crystals. Without further purification, the crystals were mixed with 100 ml of a 10% aqueous sodium hydroxide solution and the mixture was heat-refluxed for 40 minutes during which time the crystals were dissolved to form a uniform solution. The solution was treated with activated carbon while hot and filtered. The filtrate was allowed to cool and adjusted pH value to pH 2 to obtain 7.0 g of 9-chloro-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as light yellow crystals having a melting point of 282° to 286° C.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. customto precipitate light brown crystals
  4. customWithout further purification
  5. additionthe crystals were mixed with 100 ml of a 10% aqueous sodium hydroxide solution
  6. temperaturethe mixture was heat-refluxed for 40 minutes during which time the crystals
  7. dissolutionwere dissolved
  8. customto form a uniform solution
  9. additionThe solution was treated with activated carbon while hot and
  10. filtrationfiltered
  11. temperatureto cool

Sources & evidence

ORD record
ord-1e2fd4b075eb478a81d0875576b7d893
Source dataset
uspto-grants-1982_03
Patent number
US04317820

Reaction notes

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