Dimethylformamide → HCID 67449546, compound

HRID 68713Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8](=[O:19])[NH:9][N:10]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CI.[C:22](=O)([O-])[O-].[K+].[K+].CN(C)C=O>C1(C)C=CC=CC=1.O>[CH3:22][O:19][C:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 6-nitro-1-phenyl-1,2-dihydroindazol-3-one (2 g, 7.69 mmol, 1.00 equiv, 98%) in toluene (50 mL), CH3I (4.3 g, 29.68 mmol, 3.86 equiv, 98%), potassium carbonate (1.63 g, 11.58 mmol, 1.51 equiv, 98%), N,N-dimethylformamide (50 mL). The resulting solution was stirred for 1 h at 80° C. in an oil bath. The resulting solution was diluted with water (100 mL). The resulting solution was extracted with dichloromethane (2×50 mL) and the organic layers were combined, then concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). The collected fractions were combined and concentrated under vacuum to yield 3-methoxy-6-nitro-1-phenyl-1H-indazole as a yellow solid.

Workup

customInto a 100-mL 3-necked round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
extractionThe resulting solution was extracted with dichloromethane (2×50 mL)
concentrationconcentrated under vacuum
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-a0f1ba8aec9946baa96e20ba93bcd5fa
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822447B2

Reaction notes

Loading…