Hydrochloric Acid → HCID 19612110, compound

HRID 1602598Notes

Reaction equation

HRID 1602598 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:13][CH2:14][CH2:15][C:16](Cl)=[O:17].Cl>CC(C)=O>[Cl:13][CH2:14][CH2:15][C:16]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH2:8][CH2:9]1)=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 297576-NitroindolineHCID 693643-Chloropropionyl chloride

Product 1

HCID 19612110HCID 19612110, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

8.2 g (50 mmol) of 6-nitroindoline (prepared as described in Preparation 4) were dissolved in 100 ml of acetone, and 6.35 g (50 mmol) of 3-chloropropionyl chloride were added to the solution while ice-cooling, which resulted in the reaction mixture becoming a suspension. This suspension was stirred at room temperature for 1 hour, after which it was heated under reflux for 2 hours, and formed a solution. The resulting solution was cooled to room temperature, and then 10% w/v aqueous hydrochloric acid was added, and the precipitated crystals were collected by filtration. The crystals thus obtained were dried over phosphorous pentoxide in a desiccator under reduced pressure by means of a vacuum pump overnight to obtain 12.7 g (50 mmol) of the title compound as crystals, melting at 127-128° C. (yield: 100%).

Workup

  1. temperaturecooling
  2. customwhich resulted in the reaction mixture
  3. temperatureafter which it was heated
  4. temperatureunder reflux for 2 hours
  5. customformed a solution
  6. temperatureThe resulting solution was cooled to room temperature
  7. additionwas added
  8. filtrationthe precipitated crystals were collected by filtration
  9. customThe crystals thus obtained
  10. dry with materialwere dried over phosphorous pentoxide in a desiccator under reduced pressure by means of a vacuum pump overnight

Sources & evidence

ORD record
ord-9cf2f2b0e75845b5858b99142843ce1e
Source dataset
uspto-grants-1999_11
Patent number
US05981752

Reaction notes

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