Table 2.
Attempted microwave assisted coupling of ethyl 1-allyl-6-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate (4) with aniline
| Entry | Solvent | Temperature (℃) | Time (minutes) | Reaction |
|---|---|---|---|---|
| 1 | EtOH | 150 | 30 | No-reaction |
| 2 | EtOH | 150 | 60 | No-reaction |
| 3 | Ethylene glycol | 200 | 30 | Compound 7 isolated |
| 4 | DMSO | 180 | 30 | No-reaction |
| 5 | DMSO | 200 | 30 |
•Slight reaction on TLC •Mostly unreacted •Not isolatable •No appreciable change with change in reaction conditions |
| 6 | DMSO | 200 | 60 | |
| 7 | DMF | 200 | 30 | |
| 8 | DMF | 200 | 60 | |
| 9 | DMF | 220 | 60 | |
| 10 | PhOPh | 220 | 30 | No reaction |
| 11 | PhOPh | 220 | 60 | No reaction |