Pyridinium hydrochloride → HCID 178508157, compound

HRID 873033Notes

Reaction equation

[NH2:1][C:2]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]2[C:8]3[CH:19]=[CH:20][C:21]([O:23]C)=[CH:22][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.[NH+]1C=CC=CC=1>O>[NH2:1][C:2]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]2[C:8]3[CH:19]=[CH:20][C:21]([OH:23])=[CH:22][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of 3-amino-2-benzyl-8-methoxybenzo[f]quinoxaline (12) (125 mg, 396 μmol) and pyridinium hydrochloride (2.50 g, 21.6 mmol) was stirred at 190° C. (oil bath temperature) for 30 minutes and at 210° C. (oil bath temperature) for further 30 minutes. After cooling to room temperature, to the mixture was added water, the product was extracted with ethyl acetate (×3). The combined organic extract was washed successively with water (×1) and brine (×1), followed by drying over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=1/1→1/10) to give 3-amino-2-benzylbenzo[f]quinoxalin-8-ol (14, v-coelenteramine) (55.5 mg, 184 μmol, 46.5%) as an ocherous solid.

Workup

waitat 210° C. (oil bath temperature) for further 30 minutes
temperatureAfter cooling to room temperature, to the mixture
extractionthe product was extracted with ethyl acetate (×3)
extractionThe combined organic extract
washwas washed successively with water (×1) and brine (×1)
dry with materialby drying over anhydrous sodium sulfate
filtrationAfter filtration and concentration under reduced pressure
customthe residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=1/1→1/10)

Sources & evidence

ORD record: ord-65403041f82749868e871fb56f99c141
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975403B2

Reaction notes

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