Ammonium Chloride → HCID 13911926, compound

HRID 1683995Notes

Reaction equation

HRID 1683995 reaction equation
C([Mg]Br)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH3:16])=[CH:10]2.[C:17]([CH2:21][CH2:22][C:23](Cl)=[O:24])([O:19][CH3:20])=[O:18].[NH4+].[Cl-]>CCOCC.[Cl-].[Zn+2].[Cl-].ClCCl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH3:16])=[C:10]2[C:23](=[O:24])[CH2:22][CH2:21][C:17]([O:19][CH3:20])=[O:18]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 706425-Methoxy-2-methylindoleHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 178418443HCID 178418443, compound

Product 1

HCID 13911926HCID 13911926, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent4×HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethylmagnesium bromide in ether (3.0M; 7.1 mL; aldrich) was added a solution of 5-methoxy-2-methylindole (3.29 g) in ether (18 mL) at r.t. After 20 min, addition of a solution of zinc chloride in ether (1M; 20.4 mL; aldrich) resulted in the formation of a thick yellow solid. The suspension was stirred mechanically for 30 min before the rapid addition of a solution of 3-carbomethoxypropionyl chloride (2.6 mL) in ether (10 mL). The resulting mixture was vigorously stirred at r.t. for 3 h before the addition of saturated aqueous NH4Cl and dichloromethane. The two phases were separated and the organic phase was washed successively with saturated aqueous NaHCO3 and brine, dried (MgSO4) and evaporated. Trituration of the residue in ether afforded the title compound as a pink solid.

Workup

  1. customaldrich) resulted in the formation of a thick yellow solid
  2. customThe two phases were separated
  3. washthe organic phase was washed successively with saturated aqueous NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-793691d93d234f2097bcc0da1405d988
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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