Ir 435 spectrophotometer

Melting points were measured on the Griffin apparatus and were uncorrected. Determination of IR spectra was achieved using Shimadzu IR-435 spectrophotometer with KBr discs and values were obtained in cm⁻¹. ¹H NMR and ¹³C NMR were recorded on Bruker instrument at 400 MHz for ¹H NMR and 100 MHz for ¹³C NMR spectrophotometer (Faculty of Pharmacy, Mansoura University, Mansoura, Egypt), in DMSO-d₆ (as a solvent), D₂O using TMS as an internal standard and chemical shifts (δ) were expressed in parts per million (ppm) compared to internal standard, TMS (δ = 0 ppm). Coupling constant (J) values were expressed in Hertz (Hz). Signal splitting patterns were designated as follows: s, singlet; d, doublet, t, triplet; q, quartette; m, multiplet. The electron impact (EI) mass spectra were carried out using Hewlett Packard 5988 spectrometer (Palo Alto, CA) at Faculty of Science, Cairo University, Giza, Egypt. Microanalysis was calculated for C, H, N on Perkin-Elmer 2400 at the Microanalytical centre, Faculty of Science, Cairo University, Egypt and was within ±0.4% of theoretical values. The progress of the reaction and purity of products were monitored by thin layer chromatography (TLC), pre-coated plastic sheets, 0.2 mm silica gel with UV indicator (Macherey-Nagel, Düren, Germany). All used reagents and solvents were purchased from the Aldrich Chemical Company (Milwaukee, WI).

Sigma-Aldrich Company is the only supplier for all the used chemicals. Melting points were obtained on a Griffin apparatus and were uncorrected. Microanalyses for C, H, and N were carried out at the Regional Centre for Mycology and Biotechnology, Faculty of Pharmacy, Al-Azhar University. IR spectra were recorded on Shimadzu IR 435 spectrophotometer (Shimadzu Corp., Kyoto, Japan) Faculty of Pharmacy, Cairo University, Cairo, Egypt, and values were represented in cm⁻¹. ¹H NMR spectra were carried out on Bruker 400 MHz (Bruker Corp., Billerica, MA, USA) spectrophotometer, Faculty of Pharmacy, Cairo University, Cairo, Egypt. Chemical shifts were recorded in ppm on δ scale, coupling constants (J) were given in Hz, and peak multiplicities are designed as follows: s, singlet; d, doublet; dd, doublet of doublet; t, triplet; m, multiplet. ¹³C NMR spectra were carried out on Bruker 100 MHz spectrophotometer, Faculty of Pharmacy, Cairo University, Cairo, Egypt. Progress of the reactions was monitored by TLC using precoated aluminium sheet silica gel MERCK 60 F 254 and was visualised by UV lamp.
2–(1-Methyl-5–(4-methylbenzoyl)-1H-pyrrol-2-yl)acetic acid (tolmetin) (2), methyl 2–(1-methyl-5–(4-methylbenzoyl)-1H-pyrrol-2-yl)acetate (3) and 2–(1-methyl-5–(4-methylbenzoyl)-1H-pyrrol-2-yl)acetohydrazide (4) were prepared according to the reported procedures⁷ .

Melting points were obtained on a Griffin apparatus and were uncorrected. Microanalyses for C, H and N were carried out at the Regional Centre for Mycology and Biotechnology, Faculty of Pharmacy, Al-Azhar University. IR spectra were recorded on Shimadzu IR 435 spectrophotometer (Shimadzu Corp., Kyoto, Japan) Faculty of Pharmacy, Cairo University, Cairo, Egypt and values were represented in cm⁻¹. ¹H NMR spectra were carried out on Bruker 400 MHz (Bruker Corp., Billerica, MA, USA) spectrophotometer, Faculty of Pharmacy, Cairo University, Cairo, Egypt. Chemical shifts were recorded in ppm on δ scale, coupling constants (J) were given in Hz and peak multiplicities were designed as follows: s, singlet; d, doublet; dd, doublet of doublets; t, triplet; m, multiplet ¹³C NMR spectra were carried out on Bruker 100 MHz spectrophotometer, Faculty of Pharmacy, Cairo University, Cairo, Egypt. Progress of the reactions were monitored by TLC using precoated aluminium sheet silica gel MERCK 60 F 254 and was visualised by UV lamp. Compounds 1a,b were previously reported in the literature³⁸ (link) and they were prepared in this work according to the reported procedure³⁹ (link).

All chemicals were commercially available. Melting points were determined on Stuart apparatus and the values given are uncorrected. The IR spectra were recorded (KBr discs) on Shimadzu IR 435 spectrophotometer, College of Pharmaceutical Sciences and Drug Manufacturing, Misr University for Science and Technology, Egypt and the values were expressed wavenumber in cm⁻¹. The ¹H-NMR and ¹³C-NMR spectral data were obtained on Bruker 400 MHz (Bruker Corp., Billerica, MA), Microanalytical Unit, Faculty of Pharmacy, Cairo University, Cairo, Egypt, using TMS as internal standard, and chemical shift values were recorded in ppm on δ scale. The mass spectra and elemental analyses were performed at the Regional Centre for Mycology and Biotechnology, Al-Azahr University, Cairo, Egypt. The reactions were monitored by precoated aluminium sheets (TLC) in benzene-acetone (7:3 v/v).
Compounds 1^26, (link)²⁹ (link), 2^29, (link)³⁰ (link), 3^26, (link)³⁰ (link), and 5c³¹ (link) were prepared according to the reported procedure.

Melting points were determined using a Griffin apparatus and were uncorrected. IR spectra were recorded on a Shimadzu IR-435 spectrophotometer using KBr discs and values were represented in cm⁻¹. ¹H NMR and ¹³C NMR (DEPT-Q) were carried out on Bruker apparatus at 400 MHz for ¹H NMR and 100 MHz for ¹³C NMR spectrophotometer, (Faculty of Pharmacy, Beni-Suef University, Beni-Suef, Egypt), in DMSO-d₆, D₂O using TMS as an internal standard and chemical shifts were recorded in ppm on δ scale using DMSO-d₆ (2.5) as a solvent. Coupling constant (J) values were estimated in Hertz (Hz). Splitting patterns are designated as follows: s, singlet; d, doublet, t, triplet; q, quartet; dd, doublet of doublet; m, multiplet. The electron impact (EI) mass spectra were recorded on Hewlett Packard 5988 spectrometer (Palo Alto, CA). Microanalysis was performed for C, H, N on Perkin-Elmer 2400 at the Microanalytical center, Cairo University, Egypt and was within ±0.4% of theoretical values. Analytical thin-layer chromatography (TLC): pre-coated plastic sheets, 0.2 mm silica gel with UV indicator (Macherey-Nagel) was employed routinely to follow the course of reactions and to check the purity of products. All other reagents, solvents and compound 1 were purchased from the Aldrich Chemical Company (Milwaukee, WI), were used without further purification.