2-Nitrotoluene → Azoxybenzene

HRID 1754020Notes

Reaction equation

C[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=O.C([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-])=O)C.[N+](C1C=CC=CC=1)([O-])=O>>[N+:8]([C:3]1[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[N:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:13]=1)[O-:10]

Participants

Reactant 3

HCID 69442-Nitrotoluene

HCID 7416Nitrobenzene

HCID 691561-Ethyl-2-nitrobenzene

Product 1

HCID 10316Azoxybenzene

Procedure

The reduction reaction was carried out in the same manner as set forth in Example 6 except for using a mixture of 1.0 mmol of o-methyl nitrobenzene and 1.0 mmol of o-ethyl nitrobenzene instead of using nitrobenzene alone, and using 19.5 mg (the amount required for swelling of the reactant in 100%) of Polymer supported reagent-2, and thereby an azoxybenzene derivative of a symmetrical structure and an azoxybenzene derivative of an asymmetrical structure were obtained as a main product, respectively.

Workup

customThe reduction reaction

Sources & evidence

ORD record: ord-5640dc0bf2034804ae5f5c51180f0889
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169200B2

Reaction notes

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