Hydrochloric Acid → HCID 19348147, compound

HRID 1637254Notes

Reaction equation

HRID 1637254 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:17][CH2:18][C:19]([OH:21])=O)=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1.Cl.[CH2:23]([OH:25])[CH3:24]>[Zn]>[C:23]([N:8]1[C:9]2[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:19](=[O:21])[CH2:18][CH2:17][CH:6]([C:5]=23)[CH:7]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 19348183HCID 19348183, compound

Product 1

HCID 19348147HCID 19348147, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

6-chloro-2-phenylindole-3-propionic acid (19.5 g) synthesized as in Example 1, step 1 was suspended in ethanol (200 ml), and to the suspension were added zinc powder (42.5 g), then conc. hydrochloric acid (50 ml). The mixture was heated to reflux for 3 hours. In the meantime, two portions (50 ml and 20 ml) of conc. hydrochloric acid were further added 1 hour and 2 hours later respectively. After allowing the mixture to cool, the zinc was filtered off and the filtrate was diluted with water, adjusted to about pH 4 with potassium carbonate and extracted three times with ethyl acetate. The organic layers were combined, washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=9:1) to yield 4.2 g (20%) of the titled compound as a pale yellow syrup.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureto cool
  4. filtrationthe zinc was filtered off
  5. additionthe filtrate was diluted with water
  6. extractionextracted three times with ethyl acetate
  7. washwashed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-c6f3ebe657944a4bbcfbef5b105494ef
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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