Water → HCID 21938274, compound

HRID 1242140Notes

Reaction equation

HRID 1242140 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:9].[CH3:16][O:17][C:18]([C:20]1[CH:28]=[C:27]2[C:23]([C:24]([CH3:29])=[CH:25][NH:26]2)=[CH:22][CH:21]=1)=[O:19].O>C(Cl)Cl>[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:7]=1[C:8]([C:25]1[NH:26][C:27]2[C:23]([C:24]=1[CH3:29])=[CH:22][CH:21]=[C:20]([C:18]([O:17][CH3:16])=[O:19])[CH:28]=2)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 666452,4-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21938240Methyl 3-methyl-1H-indole-6-carboxylate

Product 1

HCID 21938274HCID 21938274, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminium chloride (1.72 g) is suspended in methylene chloride (50 ml), to which are added 2,4-dichlorobenzoyl chloride (1.35 g) and then 6-(methoxycarbonyl)-3-methylindole (1.00 g), and stirred at room temperature for 16 hours and then at 40° C. for 2.5 hours. The reaction mixture is poured into water with ice, and then extracted with ethyl acetate (150 ml). The organic layer is washed three times with a saturated aqueous sodium hydrogencarbonate solution (50 ml) and then with a saturated saline solution, and thereafter dried with anhydrous sodium sulfate. The drying agent is removed through filtration, and the filtrate is concentrated under reduced pressure. The resulting crystal is washed with methyl t-butyl ether and dried to obtain 2-(2,4-dichlorobenzoyl)-6-(methoxycarbonyl)-3-methylindole (71) (1.48 g).

Workup

  1. extractionextracted with ethyl acetate (150 ml)
  2. washThe organic layer is washed three times with a saturated aqueous sodium hydrogencarbonate solution (50 ml)
  3. dry with materialwith a saturated saline solution, and thereafter dried with anhydrous sodium sulfate
  4. customThe drying agent is removed through filtration
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. washThe resulting crystal is washed with methyl t-butyl ether
  7. customdried

Sources & evidence

ORD record
ord-a2ff9f06d2744601b71672c6bd6a46b7
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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