Acetyl chloride → HCID 13574130, compound

HRID 2199968Notes

Reaction equation

HRID 2199968 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[C:18](Cl)(=[O:20])[CH3:19].C(=O)([O-])O.[Na+]>ClCCl>[C:18]([C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=2)[NH:1][CH:2]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 639844Methyl indole-6-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13574130HCID 13574130, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl indole-6-carboxylate (1.01 g) in dichloromethane (30 mL) were added aluminum chloride (1.53 g) and acetyl chloride (0.5 mL) at room temperature, and then the reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (625 mg) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-743a965df74f4c1d9e7a2db7eb38c2de
Source dataset
uspto-grants-2016_06
Patent number
US09359350B2

Reaction notes

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