Diethyl Ether → Ethyl (6-methoxy-1h-indol-3-yl)(oxo)acetate

HRID 1450207Notes

Reaction equation

HRID 1450207 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1.[CH2:18]([O:20]CC)[CH3:19]>>[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C:1](=[O:5])[C:2]([O:20][CH2:18][CH3:19])=[O:3])=[CH:14][NH:15]2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 65578Oxalyl chlorideHCID 766596-Methoxy-1H-indole

Product 1

HCID 19958885Ethyl (6-methoxy-1h-indol-3-yl)(oxo)acetateYield 68%

Procedure

7.5 cm3 of oxalyl chloride are added dropwise, under argon and over a period of 30 minutes, to a solution of 8.3 g of 6-methoxyindole, prepared in accordance with the process described by P. L. Feldman and H. Rapoport, Synthesis, (1986), 736, in 100 cm3 of anhydrous diethyl ether. After stirring for two hours, the precipitate formed is separated by filtration and then suspended in 200 cm3 of ethanol. After stirring for ten hours, the product is filtered off with suction and rinsed with diethyl ether. Yield:68% Melting point: 207°-208° C.

Workup

  1. customprepared in accordance with the process
  2. customRapoport, Synthesis, (1986), 736
  3. customthe precipitate formed
  4. customis separated by filtration
  5. stirringAfter stirring for ten hours
  6. filtrationthe product is filtered off with suction
  7. washrinsed with diethyl ether

Sources & evidence

ORD record
ord-09651bc09c42452ba22434233af1cc32
Source dataset
uspto-grants-1997_02
Patent number
US05602131

Reaction notes

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