Ethanol → 3-(2-Aminoethyl)-6-fluoro-5-methoxy-1H-indole-2-carboxylic acid

HRID 2207730Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[CH2:14][CH2:13][NH:12][C:11](=[O:15])[C:7]=3[NH:8]2)=[CH:4][C:3]=1[O:16][CH3:17].C([OH:20])C.[OH-].[K+]>O>[NH2:12][CH2:13][CH2:14][C:6]1[C:5]2[C:9](=[CH:10][C:2]([F:1])=[C:3]([O:16][CH3:17])[CH:4]=2)[NH:8][C:7]=1[C:11]([OH:20])=[O:15]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 7-fluoro-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one (780 mg), ethanol (5.00 mL), and water (5.00 mL) was added potassium hydroxide (1.58 g), followed by stirring at 80° C. overnight. Potassium hydroxide (1.58 g) was added to the reaction mixture, followed by stirring at 100° C. for 6 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. The obtained residue was dissolved in water (10.0 mL), to the mixture was added acetic acid (3.00 mL), and the precipitated solid was collected by filtration and dried under reduced pressure to obtain 3-(2-aminoethyl)-6-fluoro-5-methoxy-1H-indole-2-carboxylic acid (607 mg) as a reddish brown solid.

Workup

stirringby stirring at 100° C. for 6 hours
temperatureAfter cooling to room temperature
customthe solvent was evaporated under reduced pressure
dissolutionThe obtained residue was dissolved in water (10.0 mL), to the mixture
additionwas added acetic acid (3.00 mL)
filtrationthe precipitated solid was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-8fd1e2ba7bd1484c89f0a0eb0dcab6c4
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376449B2

Reaction notes

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