Supplementary Information
Application of novel, efficient and agro-waste sourced catalyst for Knoevenagel condensation reaction
K Kantharaju* & Prashant B Hiremath
Peptide and Medicinal Chemistry Research Laboratory, Department of Chemistry, Rani Channamma University, P-B, NH-4, Belagavi 591 156, India
E-mail: kk@rcub.ac.in
Received 11 October 2018; accepted (revised) 15 November 2019
Table of Contents
1. Spectral data of representative compounds (Figures S1-S25)
260 280 300 320 340 360 380 400 420 0
1 2 3 4
Absorbance
wavelength nm
(5g) (5b) (5a)
Figure S1. UV-Vis spectra of 5a, 5b, 5gcompounds
Figure S2. FT-IR spectrum of 8-methoxy-coumarin-3-carboxylic acid (5a)
Figure S3. LC profile of 8-methoxy-coumarin-3-carboxylic acid (5a)
OVC Name
Sample 466 By Administrator Date Wednesday, July 04 2018 Description
4000 3500 3000 2500 2000 1500 1000 500450
83
14 20 25 30 35 40 45 50 55 60 65 70 75 80
cm-1
%T
1755.67cm-1, 15.59%T1679.17cm-1, 15.77%T 1607.99cm-1, 23.04%T
1419.22cm-1, 24.67%T 1472.13cm-1, 26.77%T
1404.08cm-1, 28.21%T 1225.25cm-1, 30.11%T
1101.92cm-1, 30.53%T 1283.86cm-1, 31.04%T
1206.88cm-1, 37.17%T 1575.95cm-1, 37.95%T
1371.09cm-1, 39.69%T 799.27cm-1, 40.61%T 963.20cm-1, 44.73%T 1294.72cm-1, 46.73%T
706.92cm-1, 50.23%T 3049.54cm-1, 51.55%T
3027.40cm-1, 51.62%T 3074.20cm-1, 53.81%T
1345.89cm-1, 55.31%T 1441.25cm-1, 56.18%T 2961.75cm-1, 56.26%T
740.26cm-1, 59.53%T 3424.10cm-1, 59.76%T
984.17cm-1, 61.47%T 1029.22cm-1, 62.57%T
557.92cm-1, 65.10%T 721.96cm-1, 66.83%T 1513.64cm-1, 67.51%T
631.38cm-1, 67.83%T
468.06cm-1, 73.49%T
1945.80cm-1, 75.19%T
Figure S4. LC-MS spectrum of 8-methoxy-coumarin-3-carboxylic acid (5a)
Figure S5. 1H-NMR spectrum of 8-methoxy coumarin-3-carboxylic acid (5a)
Figure S6. 13C-NMR spectrum of 8-methoxy coumarin-3-carboxylic acid (5a)
Figure S7. FT-IR spectrum of coumarin-3-carboxylic acid(5g)
Figure S8.1H-NMR spectrum of coumarin-3-carboxylic acid(5g)
470.50
574.80587.78
647.03
745.12770.44801.97833.14882.04923.85
989.341042.18
1122.111146.391165.261207.661227.26
1299.10
1374.211421.911452.371489.48
1568.371613.19
1684.25
1744.90
2781.93
2930.38
3056.41
Wed J an 31 11:06:29 2018/P11
-10 -5 0 5 10 15 20 25 30 35 40 45 50 55 60 65
%T
500 1000
1500 2000
2500 3000
3500
Wav enumbers (cm-1)
Figure S9.13C-NMR spectrum of coumarin-3-carboxylic acid(5g)
Figure S10. HR-MS spectrum of coumarin-3-carboxylic acid(5g)
Figure S11. FT-IR spectrum of 6-Bromo-coumarin-3-carboxylic acid (5b)
6BC Name
Sample 469 By Administrator Date Wednesday, July 04 2018 Description
4000 3500 3000 2500 2000 1500 1000 500450
62
11 15 20 25 30 35 40 45 50 55 60
cm-1
%T
1714.67cm-1, 11.82%T
1735.86cm-1, 12.03%T 1244.50cm-1, 12.81%T 1557.05cm-1, 14.63%T
1680.98cm-1, 15.31%T1606.95cm-1, 15.66%T
1303.38cm-1, 17.81%T
3444.86cm-1, 18.18%T
1597.87cm-1, 18.41%T
1208.68cm-1, 20.39%T 1266.97cm-1, 25.75%T
802.91cm-1, 25.94%T 1009.05cm-1, 27.32%T 1474.75cm-1, 27.65%T
1147.97cm-1, 29.69%T
820.54cm-1, 30.57%T
1064.50cm-1, 30.84%T 1135.54cm-1, 31.64%T
969.41cm-1, 32.15%T 665.81cm-1, 33.62%T 1356.71cm-1, 34.87%T
3050.40cm-1, 35.61%T 1935.21cm-1, 35.90%T
743.21cm-1, 38.02%T
3096.03cm-1, 38.27%T 2416.74cm-1, 38.89%T 1408.85cm-1, 38.66%T 605.05cm-1, 38.55%T
2218.57cm-1, 40.45%T 758.07cm-1, 40.60%T
2917.77cm-1, 40.73%T 2850.03cm-1, 41.15%T
882.92cm-1, 42.51%T
876.15cm-1, 42.55%T
517.33cm-1, 43.45%T 924.24cm-1, 45.27%T 454.52cm-1, 45.30%T
559.18cm-1, 47.44%T 473.02cm-1, 53.02%T
Figure S12. LC-MS spectrum of 6-Bromo-coumarin-3-carboxylic acid (5b)
Figure S13.1H-NMR spectrum of 6-Bromo-coumarin-3-carboxylic acid(5b)
Figure S14.1H-NMR spectrum(Extended) of 6-Bromo-coumarin-3-carboxylic acid(5b)
Figure S15.13C-NMR spectrum of 6-Bromo-coumarin-3-carboxylic acid(5b)
Figure S16.13C-NMR spectrum (Extended) of 6-Bromo-coumarin-3-carboxylic acid(5b)
Figure S17.1H-NMR spectrum of 2-(Phenylmethylene) malononitrile(6a)
Figure S18.13C-NMR spectrum of 2-(Phenylmethylene)malononitrile(6a)
Figure S19.HR-MS spectrum of 2-(Phenylmethylene)malononitrile(6a)
Figure S20.1H-NMR spectrum of [(4-methoxyphenyl)methylidene]propanedinitrile(6i)
Figure S21.1H-NMR spectrum (extended)of[(4- methoxyphenyl)methylidene]propanedinitrile(6i)
Figure S22.1H-NMR spectrum (extended) of [(4- methoxyphenyl)methylidene]propanedinitrile(6i)
Figure S23.13C-NMR spectrum of [(4-methoxyphenyl)methylidene]propanedinitrile(6i)
Figure S24.13C-NMR spectrum (extended)of[(4-methoxyphenyl)methylidene]propanedinitrile(6i)
Figure S25.13C-NMR spectrum (Extended)of [(4-methoxyphenyl)methylidene]propanedinitrile(6i)
