1H-Indol-5-amine,4-fluoro-2-methyl-(9CI)

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1H-Indol-5-amine,4-fluoro-2-methyl-(9CI) Basic information
Product Name:1H-Indol-5-amine,4-fluoro-2-methyl-(9CI)
Synonyms:1H-Indol-5-amine,4-fluoro-2-methyl-(9CI);1H-Indol-5-amine,4-fluoro-2-methyl-;4-FLUORO-2-METHYL-1H-INDOL-5-AMINE HYDROCHLORIDE;4-Fluoro-2-Methyl-1H-indol-5-aMine
CAS:398487-76-8
MF:C9H9FN2
MW:164.18
EINECS:
Product Categories:HALIDE
Mol File:398487-76-8.mol
1H-Indol-5-amine,4-fluoro-2-methyl-(9CI) Structure
1H-Indol-5-amine,4-fluoro-2-methyl-(9CI) Chemical Properties
Boiling point 343.7±37.0 °C(Predicted)
density 1.317±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka17.37±0.30(Predicted)
Appearancebrown solid
Safety Information
HS Code 2933998090
MSDS Information
1H-Indol-5-amine,4-fluoro-2-methyl-(9CI) Usage And Synthesis
Synthesis
1H-Isoindole-1,3(2H)-dione, 2-(4-fluoro-2-methyl-1H-indol-5-yl)-

398487-81-5

1H-Indol-5-amine,4-fluoro-2-methyl-(9CI)

398487-76-8

4-Fluoro-2-methyl-5-phthalimidoindole (1.2 g, 4 mmol) was used as starting material and dissolved in methanol (30 mL). Hydrazine monohydrate (260 μL, 5.3 mmol) was added to the solution and the reaction mixture was stirred for 2 h at room temperature. After completion of the reaction, the solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and filtered to remove the resulting phthalic hydrazide by-product. The filtrate was purified by fast column chromatography using a dichloromethane solution containing 0.5% methanol as eluent. The solvent in the eluate was evaporated to give a white solid containing traces of phthalic hydrazide. For further purification, the solid was dissolved in ethyl acetate and the organic phase was washed sequentially with 2N NaOH solution and brine, and then dried with anhydrous magnesium sulfate. Finally, the solvent was removed by rotary evaporation to afford 5-amino-4-fluoro-2-methylindole (500 mg, 76% yield). The product was confirmed by 1H NMR (DMSO-d6): δ 2.35 (s, 3H), 4.30 (s, 2H), 5.95 (s, 1H), 6.55 (t, 1H), 6.85 (d, 1H), 10.70 (br s, 1H). Mass spectrometry (ESI) showed the molecular ion peak m/z 165 [M+H]+.

References[1] Patent: US2003/199491, 2003, A1
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