KBS37-1 - Synthesis of 2-acetyl-quinoline

[KlementineJBS]

Link to HIRAC.

KBS37 - Synthesis of 2-acetylquinoline .docx

Reaction scheme

Outcome

79.6 mg (0.465 mmol, 76%)

[KlementineJBS]

19/07/23

1. Dissolved KBS35 (KBS35-1 - Formation of propanoate intermediate  #113 ) (149 mg, 0.61 mmol) in dioxane (3 mL)
2. Added aqueous HCl (1 M, 2.5 mL)
3. Left stirring at 100 C from ~ 4 pm

[KlementineJBS]

TLC indicated completion at ~ 10 am.

Rotovapped dioxane off.

[KlementineJBS]

4. Added some water (~ 10 mL) and extracted with ethyl acetate (3 x 10 mL)
5. Washed with NaHCO3 (20 mL)
6. Dried over mag sulphate and rotovapped down

Empty vial: 15.6699
Full vial: 15.7495
Mass: 79.6 mg (0.465 mmol, 76%)

[KlementineJBS]

H NMR

1H NMR (300 MHz, Chloroform-d) δ 8.21 (dd, J = 14.3, 8.5 Hz, 2H), 8.11 (d, J = 8.5 Hz, 1H), 7.85 (dd, J = 8.1, 1.5 Hz, 1H), 7.77 (ddd, J = 8.5, 6.9, 1.5 Hz, 1H), 7.63 (ddd, J = 8.1, 6.8, 1.2 Hz, 1H), 2.86 (s, 3H).

Doesn't appear to require columning, can be carried through to bromination step.

KBS37-1 cr_1.zip
KBS37-1 cr.pdf