Phosphoric Acid → HCID 12836919, compound

HRID 2058504Notes

Reaction equation

HRID 2058504 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 was 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 obtain 3.8 g of 9-chloro-2-methyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid. Recrystallization of the product from dimethylformamide gave 3.8 g of 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

Sources & evidence

ORD record
ord-9b4fc9e073df42e7ab1e8c8c3cead956
Source dataset
uspto-grants-1982_03
Patent number
US04317820

Reaction notes

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