Sodium Hydroxide → 1-[4-{-2-(1,1-dimethylethylamino)-ethoxy}-phenyl]-3-[1H-indol-4-yl]-2-propen-1-one

HRID 1721951Notes

Reaction equation

HRID 1721951 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=O)[C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+].[CH3:14][C:15]([NH:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[CH:24][CH:23]=1)([CH3:17])[CH3:16]>C(O)C.O>[CH3:17][C:15]([NH:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH:29]=[CH:10][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH:3]=[CH:2][NH:1]3)=[CH:24][CH:23]=1)([CH3:14])[CH3:16]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 333703Indole-4-carboxaldehydeHCID 136911921-[4-{-2-(1,1-Dimethylethylamino)-ethoxy}-phenyl]-ethanone

Product 1

HCID 542383781-[4-{-2-(1,1-dimethylethylamino)-ethoxy}-phenyl]-3-[1H-indol-4-yl]-2-propen-1-oneYield 79.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2.55 g of indole-4-carboxaldehyde and 4 ml of 50% sodium hydroxide solution was added with stirring under an inert atmosphere to a solution of 3.5 g of the product of Step B in 40 ml of ethanol and after stirring for 24 hours, the mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and the wash water was reextracted with an 8-2 chloroform-methanol mixture. The extract was washed with water and aqueous sodium chloride solution and the combined organic phases were dried over a deshydrant and were evaporated to dryness. The residue was chromatographed over silica gel and eluted with a 9-1 ethyl acetate-triethylamine mixture to obtain 4.3 g of 1-[4-{-2-(1,1-dimethylamino)-ethoxy}-phenyl]-3-[1H-indol-4-yl]-2-propen-1-one (E) melting at ≃162° C.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. washThe extract was washed with water and aqueous sodium chloride solution
  5. customthe combined organic phases were dried over a deshydrant
  6. customwere evaporated to dryness
  7. customThe residue was chromatographed over silica gel
  8. washeluted with a 9-1 ethyl acetate-triethylamine mixture

Sources & evidence

ORD record
ord-0c3e604ab6204dfc91fcba24e435a7b8
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

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