KBS33-1 - Hantzsch reaction on 2-amino-5-methylpyridine fragment

[KlementineJBS]

Reaction scheme

Outcome

[KlementineJBS]

1. Added KBS32-1 (#110 ) (250 mg, 1.49 mmol, 1.3 equiv.) and bromoketone (324.5 mg, 1.15 mmol) to a flask and added ethanol (10 mL)
2. Stirred at 80 C for ~ 5 hours
3. TLC indicated completion

(1% NH4OH, 9% MeOH, 90% MeOH)

Reaction was a light green solution with pale green/white precipitate.

4. Adjusted pH from ~ 2 to ~ 10. Attempted to collect precipitate via vacuum filtration, but precipitate was too sticky/fine and this was not effective.
5. Liquid liquid extraction on filtrate - 3 x 75 mL ethyl acetate, washed with brine and dried over mag sulphate.
6. Rotovapped down. When transferring to vial, small black spots could be seen - syringe filtered to remove and obtained a far clearer, honey coloured solution.

[KlementineJBS]

LRMS

Peaks at 269.15 [M+H]+, 291.15 [M+Na]+, 267.09 [M-H]- indicate product.

KBS33-1.d.zip KBS33-1.pdf

[KlementineJBS]

KBS33-1