Hydrochloric Acid → HCID 13958115, compound

HRID 1721955Notes

Reaction equation

HRID 1721955 reaction equation
Cl[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][CH2:12][CH2:13][C:14]2[CH:27]=[CH:26][CH:25]=[CH:24][C:15]=2[O:16][CH2:17][CH2:18][NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])[NH:4][CH:3]=1.Cl.[OH-:29].[Na+]>C(O)C.O>[CH3:21][C:20]([NH:19][CH2:18][CH2:17][O:16][C:15]1[CH:24]=[CH:25][CH:26]=[CH:27][C:14]=1[CH2:13][CH2:12][CH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:2][C:3](=[O:29])[NH:4]2)([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20030186HCID 20030186, compound

Product 1

HCID 13958115HCID 13958115, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3.76 g of the product of Step A in 94 ml of 94% ethanol and 94 ml of aqueous N hydrochloric acid was stirred under an inert atmosphere for 19 hours and was diluted with water and iced. The mixture was made alkaline by addition of 32% sodium hydroxide solution and was extracted with ethyl acetate. The organic phase was washed with water, dried over a deshydrant, filtered and evaporated to dryness. The residue was chromatographed over silica and eluted with a 9-1 ethyl acetate-triethylamine mixture to obtain 2.18 g of 1,3-dihydro-4-[3-(2-{2-[1,1-dimethylethylamino]-ethoxy}-phenyl)-propyl]-2H-indol-2-one.

Workup

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

Sources & evidence

ORD record
ord-dec2548c61b44e73855c88d22d9fd5a2
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

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