Hydrochloric Acid → Ethyl 2-(5-bromo-2-methyl-1H-indol-3-yl)acetate

HRID 1721372Notes

Reaction equation

HRID 1721372 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[C:11]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:12][CH2:13][C:14]([CH3:16])=O.Cl.O1CCOCC1>CC(O)=O>[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:14]([CH3:16])=[C:13]2[CH2:12][C:11]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10883Ethyl levulinateHCID 121574-Bromophenylhydrazine hydrochlorideHCID 312751,4-Dioxane

Product 1

HCID 10780239Ethyl 2-(5-bromo-2-methyl-1H-indol-3-yl)acetateYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-bromophenylhydrazine hydrochloride (2.23 g, 10 mmol) and ethyl levulinate (1.58 g, 11 mmol) in 10 mL HOAc was heated to reflux for 20 h. The HOAc was removed under vaccum. The residue was dissolved in 10 mL EtOH. A solution of HCl in dioxane (12 mmol, 4M solution) was added. The mixture was heated to reflux for 4 h. The mixture was concentrated under vacuum and the residue was purified by flash chromatography on silica gel, eluting with 20% EtOAc in hexane to afford 2.1 g (78%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 h
  3. customThe HOAc was removed under vaccum
  4. dissolutionThe residue was dissolved in 10 mL EtOH
  5. temperatureThe mixture was heated
  6. temperatureto reflux for 4 h
  7. concentrationThe mixture was concentrated under vacuum
  8. customthe residue was purified by flash chromatography on silica gel
  9. washeluting with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-98ed67b2a83f46d3bba7f4b527f4826d
Source dataset
uspto-grants-1996_04
Patent number
US05510368

Reaction notes

Loading…