Benzoyl chloride → HCID 86754775, compound

HRID 1602608Notes

Reaction equation

HRID 1602608 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[Cl-].[Cl-].[Al+3].C([O-])(=O)C.[K+]>ClC(Cl)C>[C:16](=[C:17]1[CH:18]=[C:19]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[C:2]([CH3:1])=[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:4]3)[CH:20]=[CH:21][CH2:22]1)=[O:23]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 517044Potassium AcetateHCID 593963Ethyl 3-methyl-1H-indole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86754775HCID 86754775, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of ethyl 3-methyl-indole-2-carboxylate (1.5 g, 7.9 mmol) and dichloroethane (20 mL) was added a solution of benzoyl chloride (2.23 g, 15.9 mmol) and dichloroethane (10 mL). Anhydrous aluminum trichloride (2.1 g, 15.8 mmol) was added in one portion and the reaction mixture was heated to reflux for 4 hours. The mixture was then poured over ice and neutralized with potassium acetate. The organic layer was separated, washed with a 5% solution of NaHCO3 and dried over MgSO4. The organic solution was then filtered, concentrated and subjected to silica gel chromatography with ethyl acetate--hexanes mixtures as eluent to provide the title compound (0.94 g). Recrystallization from benzene gave a yellow solid (mp 180-181° C.).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe organic layer was separated
  4. washwashed with a 5% solution of NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationThe organic solution was then filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6f966b9c4bca4f6ab6e3598113030ddf
Source dataset
uspto-grants-1999_11
Patent number
US05981762

Reaction notes

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