2,3-Dichlorobenzoyl chloride → (7-Ethyl-2-methyl-1H-indol-3-yl)(2,3-dichlorophenyl)methanone

HRID 890245Notes

Reaction equation

HRID 890245 reaction equation
C[Mg]I.[CH2:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([CH3:15])=[CH:11]2)[CH3:5].[Cl:16][C:17]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20].[NH4+].[Cl-]>CCOCC>[CH2:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([CH3:15])=[C:11]2[C:19]([C:18]1[CH:22]=[CH:23][CH:24]=[C:25]([Cl:26])[C:17]=1[Cl:16])=[O:20])[CH3:5]

Participants

6

Reactant 4

HCID 179442,3-Dichlorobenzoyl chlorideHCID 25517Ammonium ChlorideHCID 222505877-ethyl-2-methyl-1H-indoleHCID 178418373HCID 178418373, compound

Product 1

HCID 22250579(7-Ethyl-2-methyl-1H-indol-3-yl)(2,3-dichlorophenyl)methanoneYield 38.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

14.2 ml of 3M of MeMgI in Et2O are placed under argon and 6.78 g of 7-ethyl-2-methyl-1H-indole in 40 ml of Et2O are added dropwise. After 30 minutes, 17.84 g of 2,3-dichlorobenzoyl chloride in 60 ml of Et2O are added dropwise and the reaction medium is left stirring for 2 hours. The reaction medium is run quickly onto a saturated NH4Cl solution. The extraction is carried out with Et2O (twice) and then the organic phase is washed with a 10% NaOH solution, water and then a saturated NaCl solution. 5.5 g of the expected compound are obtained.

Workup

  1. waitthe reaction medium is left
  2. extractionThe extraction
  3. washis washed with a 10% NaOH solution, water

Sources & evidence

ORD record
ord-75d8e57cb69e4d6db7628b36c22d395f
Source dataset
uspto-grants-2006_02
Patent number
US06995184B2

Reaction notes

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