Introduction

Benzoates are the soft drugs and mostly release the parent moiety. Several of the benzoates have shown potent antimicrobial 1, 2, 3, 4 and antiseptic5 properties. In this paper the synthesis such 4-Nitro Benzoates is being reported., which shall be evaluated for antimicrobial and disinfectant activities in later series of paper.

Figure 1

CompoundsPG1 and PG2

Materials and Methods

TLC was performed on 524nm Merk TLC plates. All chemicals were of synthetic grade and 98% purisis grade. TLC was eluted with 3 different solvents to check the purity of the compounds and visualized in Iodine chamber and further in UV chamber. The 1H-NMR was performed on Bruker 400 MHZ NMR before which FT-IR was performed on Perkin Elmer spectrophotometer. The synthetic scheme for the claimed compounds has been shown in Figure 2.

Figure 2

Synthetic scheme for PG1 and PG2

3-hydroxyphenyl-4-nitrobenzoate (PG1): An equimolar solution of ethylene diamine was dissolved in 10 ml of ethanolic 1 N NaOH in round bottom flask and to it 4-nitro-benzoyl chloride was added dropwise from dropping funnel with continuous stirring for 3 hrs at room temperature. The stirring was conducted on magnetic stirrer with magnetic bead in the cresol solution. The compound that separated out after 3 hrs was dried. The compound was washed with ethanol and further dried again washed with NaOH and water and air dried.

¹HNMR (δ shift in ppm): 6.86-7.04 (2H, 6.93 (ddd, J = 8.2, 2.7, 1.8 Hz), 6.99 (ddd, J = 2.7, 1.7, 0.5 Hz)), 7.14 (1H, ddd, J = 8.1, 1.8, 1.7 Hz), 7.29 (1H, ddd, J = 8.2, 8.1, 0.5 Hz), 7.97 (2H, ddd, J = 8.6, 1.4, 0.5 Hz), 8.16 (2H, ddd, J = 8.6, 1.7, 0.5 Hz).

4-methylphenyl-4-nitrobenzoate (PG2): The procedure for the VG1 was repeated and in place of resorcinol, p-cresol was used. Rest of the procedure remains same.

¹HNMR (δ shift in ppm):  2.23 (3H, s), 6.96-7.18 (4H, 7.02 (ddd, J = 8.3, 1.4, 0.5 Hz), 7.12 (ddd, J = 8.3, 1.5, 0.5 Hz)), 7.97 (2H, ddd, J = 8.6, 1.4, 0.5 Hz), 8.16 (2H, ddd, J = 8.6, 1.7, 0.5 Hz).

Results and Discussion

The compounds complied with all spectral data and complied with IR and NMR and confirmed to be synthesised.

Conclusion

The Benzoates of 4-Nitro benzoyl chlorides were synthesized with p-cresol and resorcinol respectively.

Source of Funding

None.

Conflict of Interest

None.