Salicylaldehyde oxime → HCID 86710575, compound

HRID 1027180Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[O:9][CH3:10].[N+:11]([C:14]1[CH:18]=[CH:17][NH:16][N:15]=1)([O-:13])=[O:12].C(=NO)C1C(=CC=CC=1)O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:16]2[CH:17]=[CH:18][C:14]([N+:11]([O-:13])=[O:12])=[N:15]2)=[CH:4][C:3]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 1-bromo-4-iodo-2-methoxybenzene (3.99 g, 12.75 mmol), 3-nitro-1H-pyrazole (1.730 g, 15.30 mmol), Salicylaldoxime (0.350 g, 2.55 mmol), Cu2O (0.146 g, 1.020 mmol) and Cs2CO3 (6.23 g, 19.13 mmol) in DMF (13 mL) was degassed with N2 and heated at 95° C. overnight. After cooling to RT, the mixture was filtered through celite and rinsed with EtOAc. The filtrate was washed with water and brine. The organic solution was dried over Na2SO4, filtered and concentrated in vacuo. The residue was suspended in 5% MeOH/DCM, and the precipitate filtered, rinsed with 5% MeOH/DCM, and dried to give 2.3 g of 1-(4-bromo-3-methoxyphenyl)-3-nitro-1H-pyrazole as a white solid. The filtrate from the above work up was purified by silica gel chromatography (EtOAc/Heptane=10:90 to 50:50) to give an additional 760 mg of 1-(4-bromo-3-methoxyphenyl)-3-nitro-1H-pyrazole as a light yellow solid.

Workup

customwas degassed with N2
temperatureAfter cooling to RT
filtrationthe mixture was filtered through celite
washrinsed with EtOAc
washThe filtrate was washed with water and brine
dry with materialThe organic solution was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
filtrationthe precipitate filtered
washrinsed with 5% MeOH/DCM
customdried

Sources & evidence

ORD record: ord-4806e4de634243e1bc28cb14f19ae4d2
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729263B2

Reaction notes

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