Pyridine → Ethyl (2-methyl-1H-indol-3-yl)(oxo)acetate

HRID 549230Notes

Reaction equation

HRID 549230 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:9][C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.N1C=CC=CC=1>C(OCC)C>[CH3:9][C:10]1[NH:11][C:12]2[C:17]([C:18]=1[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 72242-MethylindoleHCID 20884Ethoxalyl chloride

Product 1

HCID 246927Ethyl (2-methyl-1H-indol-3-yl)(oxo)acetateYield 51.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of ethyl chlorooxoacetate (22.53 g, 0.165 mol) in diethyl ether (100 mL) was added over a period of 15 minutes to a cooled (0° C.) solution of 2-methylindole (19.7 g, 0.15 mol) and pyridine (14.2 g, 0.18 mol) in diethyl ether (200 mL). The reaction was stirred for two hours at 0° C. under a nitrogen atmosphere. Most of the diethyl ether had evaporated by the end of the two-hour reaction time, and a solid was present. Water (100 mL) was added, and the solid was isolated by filtration and washed with 1:1 diethyl ether/hexane. The solid (27.9 g) was then dissolved in boiling toluene (250 mL) and recrystallized upon cooling to 6° C. The crystals were isolated by filtration, washed with toluene, dried for two hours on the vacuum filter funnel, triturated with water at 75° C. for five minutes, isolated by filtration, and dried for three hours on the filter funnel to provide 17.8 g ethyl (2-methyl-1H-indol-3-yl)(oxo)acetate of as a rust-colored powder.

Workup

  1. customMost of the diethyl ether had evaporated by the end of the two-hour reaction time
  2. additionWater (100 mL) was added
  3. customthe solid was isolated by filtration
  4. washwashed with 1:1 diethyl ether/hexane
  5. dissolutionThe solid (27.9 g) was then dissolved
  6. customrecrystallized
  7. temperatureupon cooling to 6° C
  8. customThe crystals were isolated by filtration
  9. washwashed with toluene
  10. customdried for two hours on the vacuum
  11. filtrationfilter funnel
  12. customtriturated with water at 75° C. for five minutes
  13. customisolated by filtration
  14. customdried for three hours on the filter funnel

Sources & evidence

ORD record
ord-6151168ac4104d9982fd350435aaf1e2
Source dataset
uspto-grants-2011_05
Patent number
US07943636B2

Reaction notes

Loading…