Pyridine → N-(5-nitro-1H-indazol-3-yl)benzamide

HRID 497616Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[C:16]2[NH2:22])([O-:12])=[O:11].N1C=CC=CC=1>O>[N+:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][N:17]=[C:16]2[NH:22][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([O-:12])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

N-(5-Nitro-1H-indazol-3-yl)benzamide may be obtained in the following manner: 0.39 cm3 of benzoyl chloride is added dropwise to a solution of 0.6 g of 5-nitro-1H-indazole-3-amine and 5 cm3 of pyridine, cooled to 0° C. The medium is returned to a temperature in the region of 20° C. and stirred for 18 hours. After addition of 20 cm3 of distilled water, the medium is extracted with 20 cm3 and 10 cm3 of ethyl acetate. The organic phases are combined, dried over magnesium sulphate, filtered and concentrated by evaporation under reduced pressure. The residue thus obtained is purified by chromatography on a column of silica with a dichloromethane/methanol mixture (99/1 by volume) as eluent. 0.9 g of N-(5-nitro-1H-indazol-3-yl)benzamide is thus obtained in the form of an orange-coloured solid melting at 231° C.

Workup

customis returned to a temperature in the region of 20° C.
extractionthe medium is extracted with 20 cm3 and 10 cm3 of ethyl acetate
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationconcentrated by evaporation under reduced pressure
customThe residue thus obtained
customis purified by chromatography on a column of silica with a dichloromethane/methanol mixture (99/1 by volume) as eluent

Sources & evidence

ORD record: ord-dc929335049143bdb6ee36b3bd35a38d
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949579B2

Reaction notes

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