Potassium Carbonate → Methyl 1H-indole-2-carboxylate

HRID 1677799Notes

Reaction equation

HRID 1677799 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13]C)=[O:11].C([O-])([O-])=O.[K+].[K+].CCOCC.CCCCCCC>CO.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 73125Ethyl indole-2-carboxylateHCID 21897273Diethylether heptane

Product 1

HCID 70992Methyl 1H-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Add to ethyl indole-2-carboxylate 1 (42.3 mmol) in MeOH (50 mL), K2CO3 (1.20 equiv., 50.7 mmol) and stir the suspension with heating to 55° C. for 1 h. Monitor the reaction by tlc (ether/heptane) and when complete concentrate the reaction in vacuo, dilute with H2O and stir for 15 min. Collect the solid by filtration and dry under vacuum at 65° C. for 3 h to afford methyl indole-2-carboxylate 2.

Workup

  1. concentrationcomplete concentrate
  2. customthe reaction in vacuo
  3. stirringstir for 15 min
  4. customCollect the solid
  5. filtrationby filtration
  6. customdry under vacuum at 65° C. for 3 h

Sources & evidence

ORD record
ord-3f6bee9585c8427c9fcc9965114b96de
Source dataset
uspto-grants-2011_08
Patent number
US08008340B2

Reaction notes

Loading…