Acetic Acid → HCID 21273612, compound

HRID 1382843Notes

Reaction equation

HRID 1382843 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH:7]([OH:29])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[O:28])[CH2:17][CH2:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2)([CH3:4])[CH3:3].[Cl:30]N1C(=O)CCC1=O.C(O)(=O)C.[OH-].[Na+]>O>[Cl:30][C:21]1[C:20]2[C:24](=[CH:25][CH:26]=[CH:27][C:19]=2[CH2:18][CH2:17][C:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][CH2:8][CH:7]([OH:29])[CH2:6][NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:28])[NH:23][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 3066297HCID 3066297, compound

Product 1

HCID 21273612HCID 21273612, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.6 g of 1-[2-[3-(1,1-dimethylethylamino)-2-hydroxypropoxy]-phenyl]-3-(1H-indol-4-yl)-1-propanone, 3 g of N-chlorosuccinimide and 170 ml of acetic acid was stirred at room temperature for 2 hours and was then diluted with water. The mixture was made alkaline by addition of sodium hydroxide and was extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica and eluted with a 6-3-1 chloroform-acetone-triethylamine mixture to obtain 6.37 g of 3-(3-chloro-1H-indol-4-yl)-1-[2-[3-(1,1-dimethylethylamino)-2-hydroxypropoxy]-phenyl]-1-propanone.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica
  6. washeluted with a 6-3-1 chloroform-acetone-triethylamine mixture

Sources & evidence

ORD record
ord-5b990beb99b44bfc99be92bb37084047
Source dataset
uspto-grants-1989_02
Patent number
US04808609

Reaction notes

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