Methyl 4-methoxy-2,3-dihydro-1H-indole-2-carboxylate → 4-Methoxyindoline-2(r/s)-carboxylic acid butylamide

HRID 2185679Notes

Reaction equation

HRID 2185679 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH:6]([C:12]([O:14]C)=O)[NH:7]2>C(N)CCC>[CH2:6]([NH:7][C:12]([CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])[NH:7]1)=[O:14])[CH2:5][CH2:4][CH3:3]

Participants

3

Reactant 1

HCID 22451269Methyl 4-methoxy-2,3-dihydro-1H-indole-2-carboxylate

Product 1

HCID 777521434-Methoxyindoline-2(r/s)-carboxylic acid butylamide

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

Methyl 4-methoxyindoline-2(R/S)-carboxylate (0.89 g, 4.3 mmol) was dissolved in butylamine (40 ml) under nitrogen and the solution was then stirred at reflux for three hours. After cooling the mixture, the remaining butylamine was removed under vacuum. The crude product was recrystallized from diethyl ether in order to give an off-white solid.

Workup

  1. temperatureat reflux for three hours
  2. temperatureAfter cooling the mixture
  3. customthe remaining butylamine was removed under vacuum
  4. customThe crude product was recrystallized from diethyl ether in order
  5. customto give an off-white solid

Sources & evidence

ORD record
ord-837d7804bcd34b97921f7f0a472d2369
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

Loading…