Closed KlementineJBS closed 1 year ago
TLC at 4.30 pm indicated formation of product but SM was still present as indicated by positive staining with bromocresol green.
Turned up heat to 70 C as no condensation was visible and left overnight.
TLC at 9 am indicated that reaction was still not yet complete. Worked up anyway - not sure how sensitive the bromocresol is, and no UV showed up on the baseline for RM.
Empty vial: 15.8551 Full vial: 16.3173 Mass: 462.2 mg (2.47 mmol, 82%)
Hard brittle solid, pale beige in colour.
1H NMR (300 MHz, Chloroform-d) δ 8.29 (dd, J = 8.5, 1.9 Hz, 2H), 8.18 (d, J = 8.5 Hz, 1H), 7.86 (dd, J = 8.2, 1.5 Hz, 1H), 7.77 (ddd, J = 8.4, 6.8, 1.5 Hz, 1H), 7.63 (ddd, J = 8.1, 6.9, 1.2 Hz, 1H), 4.07 (s, 3H).
Compound was re-dissolved by chloroform from NMR and rotovapped down - formed white crystalline solid.
Link to HIRAC and original method.
KBS34 - Synthesis of methyl quinoline-2-carboxylate.docx
Reaction scheme
Outcome
462.2 mg (2.47 mmol, 82%)