5-Methoxyindole → HCID 21912015, compound

HRID 1246940Notes

Reaction equation

HRID 1246940 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:9](=C[CH:11]=1)[NH:8][CH:7]=[CH:6]2.[C:12](Cl)(=[O:16])[C:13](Cl)=O.C(=O)([O-])[O-].[NH4+:22].[NH4+:23]>C(OCC)C>[NH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[CH:11][N:22]=2)[C:6]([CH2:13][C:12]([NH2:23])=[O:16])=[CH:7]1

Participants

5

Reactant 3

HCID 138725-MethoxyindoleHCID 65578Oxalyl chlorideHCID 517111Ammonium Carbonate

Product 1

HCID 21912015HCID 21912015, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-methoxyindole (2.50 g, 17.0 mmol) in 50 mL of anhydrous diethyl ether cooled to 0° C. was added oxalyl chloride (1.63 mL, 18.68 mmol) and subsequently warmed to room temperatue. After 3.5 hours the solution was cooled to 0° C. and 50 mL of an aqueous solution of ammonium carbonate was added. After stirring overnight the precipitate was filtered off and washed with water, isopropanol and diethyl ether to afford the desired acetamide in 78% yield as a bright yellow solid.

Workup

  1. temperaturesubsequently warmed to room temperatue
  2. filtrationwas filtered off
  3. washwashed with water, isopropanol and diethyl ether

Sources & evidence

ORD record
ord-7d6a7e41812c44979147bf2869526e54
Source dataset
uspto-grants-2006_10
Patent number
US07129250B2

Reaction notes

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