2,4-Dichlorobenzoyl chloride → HCID 22388197, compound

HRID 1072798Notes

Reaction equation

HRID 1072798 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[C:8](Cl)=O.[CH3:16][C:17]1[CH:18]=[C:19]2[N:24]([CH:25]=1)[CH:23]=[C:22]([C:26]([O:28][CH3:29])=[O:27])[CH:21]=[CH:20]2>ClCCl>[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[CH2:8][C:25]1[N:24]2[C:19]([CH:20]=[CH:21][C:22]([C:26]([O:28][CH3:29])=[O:27])=[CH:23]2)=[CH:18][C:17]=1[CH3:16]

Participants

5

Reactant 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22387856HCID 22387856, compound

Product 1

HCID 22388197HCID 22388197, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of anhydrous aluminum chloride (3.18 g) in dichloromethane (19 ml) was added 2,4-dichlorobenzoyl chloride (2.93 g) under ice-cooling, and the mixture was stirred for 10 min. To this solution was added methyl 2-methylindolizine-6-carboxylate (1.89 g) and the mixture was stirred for 4 hr at room temperature. The reaction mixture was slowly poured into ice water and the resulting product was extracted with ethyl acetate. The organic layer was washed successively with water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the objective compound (2.39 g) as a pale-yellow solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 4 hr at room temperature
  3. extractionthe resulting product was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water
  5. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-0b931ffc5bc948249a3f7ac7b28ee37a
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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