Ethanol → HCID 12911931, compound

HRID 2058497Notes

Reaction equation

HRID 2058497 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:24]=[C:23]([Cl:25])[CH:22]=[C:21]2[C:16]=1[CH2:17][CH2:18][CH2:19][NH:20]2.C(O)C.[OH-].[Na+]>O>[Cl:14][C:15]1[C:16]2=[C:21]3[N:20]([CH2:19][CH2:18][CH2:17]2)[CH:4]=[C:5]([C:6]([OH:8])=[O:7])[C:11](=[O:13])[C:22]3=[C:23]([Cl:25])[CH:24]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 16244392HCID 16244392, compoundHCID 858292113-Ethoxy-2-ethoxycarbonylprop-2-enoate

Product 1

HCID 12911931HCID 12911931, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

3.1 g of ethyl ethoxymethylenemalonate was added to 2.7 g of 5,7-dichloro-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 100 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 to a pH of 2 to obtain 2.7 g of 8,10-dichloro-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as light yellow crystals having a melting point of 300° to 304° C.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. customto precipitate light brown crystals
  4. customWithout further purification the crystals
  5. additionwere 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-ad99f822c52a4299bf14716755c51a2e
Source dataset
uspto-grants-1982_03
Patent number
US04317820

Reaction notes

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