Further photochemical hydrogenation of nitro compounds

    In our previous application note (No. 41) we reported on a green and efficient photochemical route to the reduction of 3-nitro-acetophenone to 3-amino-acetophenone.

    Challenged to show the broad applicability of the photochemical reduction using the low cost and green TiO2 photo catalyst we set out to extend this work to optimize the reduction of 3 further Nitro compounds. The compounds chosen exhibit a range of different reactivity, one compound was further chosen as a ‘real-world’ example, 4-(2-fluoro-4-nitrophenyl)morpholine being a key intermediate used in the synthesis of the oxazolidinone antibiotic Linezolid (Pfizer brand name ZYVOX®)

    All 4 compounds are shown to be readily reduced and once optimized the photochemical method in all cases provided excellent yields of the desired product.

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    3-Nitro-acetophenone to 3-amino-acetophenone

    photochemical-reductions01

    4-Nitroanisole to p-anisidine

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    2,4-Dichloronitrobenzene to 2,4-dichloroaniline

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    Linezolid intermediate, 4-(2-fluoro-4-nitrophenyl)morpholine to 3-Fluoro-4-(4-morpholinyl)aniline

    photochemical-reductions04

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