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 |