Isobutyryl chloride → HCID 10245893, compound

HRID 1110027Notes

Reaction equation

HRID 1110027 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][C:6]1[N:16]2[C:17]3[C:12]([CH2:13][CH2:14][CH2:15]2)=[CH:11][CH:10]=[CH:9][C:8]=3[C:7]=1[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].[C:24](Cl)(=[O:28])[CH:25]([CH3:27])[CH3:26]>C(Cl)(Cl)Cl>[CH3:26][CH:25]([CH3:27])[C:24]([C:10]1[CH:11]=[C:12]2[C:17]3=[C:8]([C:7]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:6]([CH3:5])[N:16]3[CH2:15][CH2:14][CH2:13]2)[CH:9]=1)=[O:28]

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 10264445HCID 10264445, compound

Product 1

HCID 10245893HCID 10245893, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
10 °C

Procedure

63 g of aluminum trichloride were suspended in 150 ml of chloroform at a temperature of 10° C. A mixture of ethyl 5,6-dihydro-2-methyl-4H-pyrrolo[3,2,1-ij]quinoline-1-acetate and 26.3 g of isobutyryl chloride in 150 ml of chloroform was added to the suspension while the temperature was maintained at 10° C. The reaction mixture was stirred at room temperature for hour, then heated under reflux for 4 hours and kept at room temperature for a further 12 hours. A further 10 g of aluminum chloride were then added, and the mixture was heated under reflux for a further hour. The reaction mixture was worked up by pouring it onto ice and then extracting with dichloromethane. The organic phase was washed with dilute aqueous sodium hydroxide solution, then washed with water until neutral, dried and concentrated. 80 g of crude product were obtained, which was purified by chromatography on a silica gel column using dichloromethane as the eluent. 42.5 g of ethyl 5,6-dihydro-8-(2-methyl-1-oxopropyl)-2-methyl-4H-pyrrolo[3,2,1-ij]quinoline-1-acetate were obtained.

Workup

  1. additionwas added to the suspension while the temperature
  2. temperatureheated
  3. temperatureunder reflux for 4 hours
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for a further hour
  6. additionby pouring it onto ice
  7. extractionextracting with dichloromethane
  8. washThe organic phase was washed with dilute aqueous sodium hydroxide solution
  9. washwashed with water until neutral,
  10. customdried
  11. concentrationconcentrated
  12. custom80 g of crude product were obtained
  13. customwhich was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-73a9997e23a7423f961cb043fc31ce74
Source dataset
uspto-grants-1994_06
Patent number
US05324725

Reaction notes

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