Phosphoric Acid → HCID 12836918, compound

HRID 1649423Notes

Reaction equation

HRID 1649423 reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8]CC)=[O:7])C.[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH2:19][CH2:20][NH:21]2.P(=O)(O)(O)O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>O.C(O)C>[Cl:16][C:17]1[C:18]2[CH2:19][CH2:20][N:21]3[C:22]=2[C:23]([C:11](=[O:13])[C:5]([C:6]([OH:8])=[O:7])=[CH:4]3)=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 30163064-Chloroindoline

Product 1

HCID 12836918HCID 12836918, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 4.4 g of diethyl ethoxymethylenemalonate was added 3 g of 4-chloroindoline and the mixture was heated on an oil bath at 110° to 120° C. during which time liberation of ethanol was observed. 20 g of polyphosphoric acid prepared from 10 g of phosphoric acid and 10 g of phosphorus pentoxide was added thereto and the mixture was heated on an oil bath at 130° to 140° C. for 40 minutes. After completion of the reaction, the mixture was allowed to cool to 60° C., poured into water and rendered neutral with a 10% aqueous sodium hydroxide solution. The crystals precipitated were collected by filtration and washed with water. The crystals thus-treated were mixed with 50 ml of a 10% aqueous sodium hydroxide solution and the mixture was heat-refluxed on an oil bath for 1 hour. As the reaction proceeded the mixture changed to a uniform solution. The solution was treated with activated carbon while hot followed by filtration. The filtrate was rendered acidic with concentrated hydrochloric acid to precipitate crystals. Recrystallization of the crystals from dimethylformamide gave 3.5 g of 9-chloro-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid as white needles having a melting point of 307.5° C. (decomposed).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated on an oil bath at 130° to 140° C. for 40 minutes
  3. customAfter completion of the reaction
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. additionThe crystals thus-treated
  8. additionwere mixed with 50 ml of a 10% aqueous sodium hydroxide solution
  9. temperaturethe mixture was heat-refluxed on an oil bath for 1 hour
  10. additionThe solution was treated with activated carbon
  11. filtrationwhile hot followed by filtration
  12. customto precipitate crystals
  13. customRecrystallization of the crystals from dimethylformamide

Sources & evidence

ORD record
ord-afad339de43a4f47b8bd3872c7a6bfca
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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