Reference of 15362-40-0, The chemical industry reduces the impact on the environment during synthesis 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, I believe this compound will play a more active role in future production and life.
Reference of 15362-40-0, The chemical industry reduces the impact on the environment during synthesis 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, I believe this compound will play a more active role in future production and life.
Pyrrole-2-carboxaldehyde (1 mmol) was treated with benzyl bromide (1.5 mmol) in the presence of NaH (1.5 mmol) in DMF (solvent) at 0 C for 15 min, the progress of the reaction was monitored with TLC and the reaction was shifted to room temp for another 15 min. After completion, the reaction was quenched by adding water and the crude product was isolated by extraction with ethyl acetate (2 x 50 ml), the organic layers were combined, dried over Na2SO4 and distilled in vacuum to give N-benzylpyrrole-2-carboxaldehyde (A) which was further purified by column chromatography using ethyl acetate: hexane (1:50). N-benzylpyrrole-2-carboxaldehyde (A, 1 mmol) was reacted with 1-(2,6-dichlorophenyl)-2-indolinone (1.2 mmol) in the presence of piperidine (0.2 mmol) in CHCl3/ DMF under microwave irradiations at 100 C for 1h. The progress of the reaction was monitored with TLC. After completion, the reaction was worked up by adding water and extraction with chloroform (2 x 50 ml). Combined organic layers were dried over Na2SO4 and distilled in vacuum to give crude product 3a which was purified by column chromatography using ethyl acetate:hexane (3:50) as eluent. Yellow Solid, yield 62%, mp 153-155 C; IR (KBr): 3059, 2925, 1695, 1599, 1485, 1365; 1H NMR (500 MHz, CDCl3, 25 C, TMS) delta: 5.41 (s, 2H, CH2), 6.40-6.41 (m, 2H, ArH), 7.04 (t, 1H, J = 7.5 Hz, ArH), 7.07 (s, 1H, ArH), 7.13 (t, 1H, J = 7.6 Hz, ArH), 7.19 (d, 2H, J = 7.4 Hz, ArH), 7.29-7.34 (m, 2H, ArH), 7.36-7.41 (m, 3H, ArH), 7.47 (s, 1H, =CH), 7.52 (d, 2H, J = 8.09 Hz, ArH), 8.49 (dd, 1H, J = 4.13 Hz, 1.29 Hz, ArH); 13C NMR (125 MHz, CDCl3, normal/DEPT-135) delta: 51.3 (-ve, CH2), 108.6 (+ve, CH), 110.7, (+ve, CH), 117.1 (ArC), 117.8 (+ve,CH), 121.9 (+ve, CH), 122.1 (+ve, CH), 123.0 (+ve, CH), 125.2 (ArC), 126.2 (+ve, CH), 126.9 (+ve, CH), 127.1 (+ve, CH), 128.0 (+ve, CH), 128.7 (ArC), 128.8 (+ve, CH), 128.9 (+ve, CH), 129.1 (+ve, CH), 129.2 (+ve, CH), 130.1 (+ve, CH), 131.4 (ArC), 135.9 (ArC), 137.3 (ArC), 139.2 (ArC), 164.8 (C=O); HRMS (ESI) m/z for C26H18Cl2N2O [M+H]+ calcd. 445.0868, found 445.0817.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Kaur, Jagroop; Kaur, Baljit; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 28; 2; (2018); p. 129 – 133;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem