Sodium Hydroxide → HCID 54471464, compound

HRID 1721947Notes

Reaction equation

HRID 1721947 reaction equation
[OH-].[Na+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH:12]=O)[C:6]=2[CH:5]=[CH:4]1.[CH3:14][C:15]([NH:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29](=[O:31])[CH3:30])([CH3:17])[CH3:16]>C(O)C.O>[CH3:17][C:15]([NH:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29](=[O:31])[CH:30]=[CH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][NH:3]2)([CH3:14])[CH3:16]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 333703Indole-4-carboxaldehydeHCID 20030191HCID 20030191, compound

Product 1

HCID 54471464HCID 54471464, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3 ml of 50% sodium hydroxide solution and then 1.484 g of indole-4-carboxaldehyde were added to a solution of 2.55 g of 1-[2-{3-(1,1-dimethylethylamino)-propoxy}-phenyl]-ethanone in 35 ml of ethanol and the mixture was stirred under an inert atmosphere for 20 minutes. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over a deshydrant, filtered and evaporated to dryness under reduced pressure. The residue was chromatographed over silica and eluted with a 9-1 ethyl acetate-triethylamine mixture to obtain 2.804 g of 1-[2-{3-(1,1-dimethylethylamino)-propoxy}-phenyl]-3-[1H-indol-4-yl]-2-propen-1-one.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried over a deshydrant
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica
  7. washeluted with a 9-1 ethyl acetate-triethylamine mixture

Sources & evidence

ORD record
ord-7befd607d4374ac08b47898d793b08d9
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

Loading…