Hydrochloric Acid → HCID 54535298, compound

HRID 361630Notes

Reaction equation

HRID 361630 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]2[C:5]=1[CH:6]=[C:7]([C:14]([O-:16])=[O:15])[NH:8]2.[C:17](Cl)(=[O:19])[CH3:18].Cl.[CH3:22]N(C=O)C>>[C:17]([N:8]1[C:9]2[C:5](=[C:4]([CH3:3])[CH:12]=[CH:11][C:10]=2[CH3:13])[CH:6]=[C:7]1[C:14]([O:16][CH3:22])=[O:15])(=[O:19])[CH3:18]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide3×HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 7022949HCID 7022949, compound

Product 1

HCID 54535298HCID 54535298, compoundYield 22%

Procedure

A suspension of 0.11 g (4.13 mmol) of sodium hydride in 10 ml of anhydrous DMF was prepared. A solution of 0.8 g (3.94 mmol) of 4,7-dimethylindole-2-carboxylate in 10 ml of anhydrous DMF was added thereto dropwise at 0° C. over a period of 30 minutes and the reaction mixture was stirred for 1 hour. Then a solution of 0.47 g (4.33 mmol) of acetyl chloride in 0.4 ml of anhydrous DMF was added dropwise, and the reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was added dropwise to 300 ml of ice water, acidified with 1N HCl aqueous solution and extracted with ethyl acetate three times. The ethyl acetate solutions were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to provide 212 mg of white crystals.

Workup

  1. customwas prepared
  2. stirringthe reaction mixture was stirred at room temperature for 12 hours
  3. extractionextracted with ethyl acetate three times
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7ddaafd0bb944d66ae58a7c33aed2353
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

Loading…