Pyridine → 1-Acetyl-1H-indole-3-carbaldehyde

HRID 1854669Notes

Reaction equation

HRID 1854669 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.N1C=CC=CC=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>ClCCl.C(OCC)(=O)C>[C:18]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1)(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10256Indole-3-Carboxaldehyde

Product 1

HCID 899151-Acetyl-1H-indole-3-carbaldehydeYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-indole-3-carboxaldehyde (300 mg, 2.07 mmol) in 6.2 mL of dry dichloromethane were added pyridine (0.34 mL, 4.2 mmol), acetic anhydride (0.59 mL, 6.2 mmol), and N,N-dimethylaminopyridine (20 mg, 0.16 mmol) at room temperature, successively. After being stirred at room temperature for 2 h, the reaction mixture was diluted with ethyl acetate. The solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting solid was rinsed with diethyl ether/hexane to obtain the title compound as a white powder (235 mg, 77%).

Workup

  1. washThe solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe resulting solid was rinsed with diethyl ether/hexane

Sources & evidence

ORD record
ord-86319af6314345539db73e5a4a67568a
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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