Chloroacetyl chloride → HCID 19003095, compound

HRID 2372773Notes

Reaction equation

HRID 2372773 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][C:7](Cl)=[O:8].[CH3:10][N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[CH2:20][CH2:21][C:22](=[O:23])[C:12]1=2>C(Cl)Cl>[Cl:5][CH2:6][C:7]([C:16]1[CH:17]=[CH:18][C:19]2[N:11]([CH3:10])[C:12]3[C:22](=[O:23])[CH2:21][CH2:20][C:13]=3[C:14]=2[CH:15]=1)=[O:8]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 6451240Aluminum(III) Chloride2×HCID 118162821,4-Dihydro-4-methylcyclopent[b]indol-3(2H)-one

Product 1

HCID 19003095HCID 19003095, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Aluminum chloride (8.5 g) was suspended in CH2Cl2 (20 ml) at 0° C., chloroacetyl chloride (7.2 g) was slowly added and the mixture was stirred for 5 minutes. This mixture was added dropwise to a stirred solution of 1,4-dihydro-4-methyl-cyclopent[b]indol-3(2H)-one (6.0 g) in 100 ml CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 45 minutes and thereafter an additional equivalent of preformed solution of aluminum chloride and chloroacetyl chloride in methylene chloride was introduced in a dropwise manner. After 30 minutes the reaction mixture was slowly poured into a stirred ice/water mixture. The layers were separated and the CH2Cl2 layer was washed with NaHCO3, dried (Na2SO4) and concentrated to an oil. Purification by flash chromatography on silica gel eluting with hexane/acetone provided 7-chloroacetyl-1,4-dihydro-4-methyl-cyclopent[b]indol-3(2H)-one (4.5 g).

Workup

  1. stirringThe mixture was stirred at 0° C. for 45 minutes
  2. customThe layers were separated
  3. washthe CH2Cl2 layer was washed with NaHCO3
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to an oil
  6. customPurification by flash chromatography on silica gel eluting with hexane/acetone

Sources & evidence

ORD record
ord-946a528ddac642d0a6a8db89be662978
Source dataset
uspto-grants-1992_03
Patent number
US05100891

Reaction notes

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