Hydrochloric Acid → HCID 19612110, compound

HRID 965424Notes

Reaction equation

HRID 965424 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-7614d70586af48109ace2935bea37ac5
Source dataset
uspto-grants-1998_06
Patent number
US05773618

Reaction notes

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