Nitric Acid → HCID 178422360, compound

HRID 2299154Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1.[N+:11]([O-])([OH:13])=[O:12]>>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]2[N:6]=[CH:7][NH:8][C:4]=2[CH:3]=1

Participants

Reactant 2

HCID 944Nitric Acid

HCID 119795-Methylbenzimidazole

Product 1

HCID 178422360HCID 178422360, compoundYield 17%

Conditions

Temperature: -15 °C

Procedure

To a solution of 20 ml of fuming nitric acid was added 5-methylbenzimidazole (1.6 g, 12 mmol) slowly over 0.5 h and reaction mixture was stirred for 3 h at −15° C. During addition of substrate, reaction temperature was kept below −10° C. Sticky reaction mixture was then poured into ice water to form a yellow precipitation, which was collected and dried in vacuo to provide 0.37 g (2.1 mmol, 17%) of 5-methyl-6-nitrobenzimidazole. The nitrobenzimidazole was converted to the corresponding amine (0.32 g, 95%) on hydrogenation (H2, Pd/C).

Workup

customreaction mixture
additionDuring addition of substrate, reaction temperature
customwas kept below −10° C
customSticky reaction mixture
customto form
customa yellow precipitation, which
customwas collected
customdried in vacuo

Sources & evidence

ORD record: ord-ff6b0bddc4da403aa53f8399798a6be5
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495583B1

Reaction notes

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