Hydrochloric Acid → HCID 67289453, compound

HRID 511844Notes

Reaction equation

HRID 511844 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C@@H:11]2[CH2:13][C@H:12]2[C:14]([O:16]CC)=[O:15])=[CH:3]1.[OH-].[Na+].Cl>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C@@H:11]2[CH2:13][C@H:12]2[C:14]([OH:16])=[O:15])=[CH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67289892HCID 67289892, compound

Product 1

HCID 67289453HCID 67289453, compoundYield 141.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl trans-2-(1-methyl-1H-indol-3-yl)cyclopropanecarboxylate (20 mg, 0.082 mmol) and 2 mol/L aqueous sodium hydroxide solution (0.20 mL, 0.40 mmol) in methanol (3 mL) was stirred at 60° C. for 3 hours. After cooling to room temperature, 2 mol/L hydrochloric acid (0.20 mL, 0.40 mmol) was added, and the solvent was removed in vacuo. To the residue was added THF (2 mL) and filtered off. The filtrate was concentrated in vacuo to give 25 mg of the title compound as a pale yellow oil. This was used for the next step without purification:

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed in vacuo
  3. additionTo the residue was added THF (2 mL)
  4. filtrationfiltered off
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-00741ac55c814d689f4f115825f0c116
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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