Phosphoric Acid → HCID 12836919, compound

HRID 1649424Notes

Reaction equation

HRID 1649424 reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8]CC)=[O:7])C.[CH3:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[Cl:26])[NH:18]1.P(=O)(O)(O)O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>>[Cl:26][C:23]1[C:24]2[CH2:25][CH:17]([CH3:16])[N:18]3[C:19]=2[C:20]([C:11](=[O:13])[C:5]([C:6]([OH:8])=[O:7])=[CH:4]3)=[CH:21][CH:22]=1

Participants

6

Reactant 5

HCID 1004Phosphoric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 204796784-Chloro-2-methyl-2,3-dihydro-1H-indole

Product 1

HCID 12836919HCID 12836919, compoundYield 71.1%

Conditions

Temperature
60 °C

Procedure

4.4 g of diethyl ethoxymethylenemalonate was added to 3.4 g of 2-methyl-4-chloroindoline and the mixture was heated on an oil bath at 110° to 120° C. for 40 minutes. 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 1 hour. After completion of the reaction, the mixture was allowed to cool to 60° C., poured into ice 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 product from dimethylformamide gave 3.8 g of 9-chloro-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid as white needles having a melting point of 288° to 290° C.

Workup

  1. temperaturethe mixture was heated on an oil bath at 110° to 120° C. for 40 minutes
  2. additionwas added
  3. temperaturethe mixture was heated on an oil bath at 130° to 140° C. for 1 hour
  4. customAfter completion of the reaction
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. additionThe crystals thus treated
  9. additionwere mixed with 50 ml of a 10% aqueous sodium hydroxide solution
  10. temperaturethe mixture was heat-refluxed on an oil bath for 1 hour
  11. additionThe solution was treated with activated carbon
  12. filtrationwhile hot followed by filtration
  13. customto precipitate crystals
  14. customRecrystallization of the product from dimethylformamide

Sources & evidence

ORD record
ord-fc6d579147004cd78d5555b807e8256f
Source dataset
uspto-grants-1983_11
Patent number
US04416884

Reaction notes

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