Reaction #2487397

Reaction equation

4-cyanobenzoyl chloride

NaH

3-(hydroxymethyl)pyridine-2(1H)-one

→

(1,2-dihydro-2-oxopyridin-3-yl)methyl 4-cyanobenzoate

Yield 28.5%

Solvents

THF

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe reaction was stirred
3. 3
   Temperaturewith gentle heating for 48 hours
4. 4
   OtherThe reaction was quenched with 20 mL of and
5. 5
   Washwas washed with ethyl acetate (4×20 mL)
6. 6
   WashThe organic layer was washed with brine (3×20 mL)
7. 7
   Dryingbefore being dried of MgSO4
8. 8
   OtherThe solvent was evaporated in vacuo
9. 9
   Otherto produce a white solid
10. 10
    OtherThe product was purified with silica gel column chromatography

Procedure

In Example 3, 0.0723 g of 60% NaH was dispersed in mineral oil (0.64 mmol) and was suspended in 50 mL of THF in a 100 mL RBF under the presence of argon gas. Then, 0.2026 g (1.62 mmol) of 3-(hydroxymethyl)pyridine-2(1H)-one was slowly added into the solution. This solution was stirred for 30 min with gentle heating before 0.2661 g (1.61 mmol) of 4-cyanobenzoyl chloride was added. The reaction was stirred with gentle heating for 48 hours. The reaction was quenched with 20 mL of and was washed with ethyl acetate (4×20 mL) and the organic layers combined. The organic layer was washed with brine (3×20 mL) before being dried of MgSO4. The solvent was evaporated in vacuo to produce a white solid. The product was purified with silica gel column chromatography using 10% methanol in dichloromethane as eluent. The yield of the reaction was 0.1175 g (28.54% yield). MP: 200-203° C. IR (cm−1): 3406.04 (m, broad), υ (O—H), 3113.07 (m, broad), υ (N—H), 1728.71 (m), υ (C═O), 1617.96 (s), υ (C═C aromatic). 1H NMR (DMSO-d6, 500 MHz) δ: 5.17 (s, 2H), 6.23 (t, J=6.6 Hz, 1H), 7.42 (dd, J=4.5, 2.0 Hz, 1H), 7.63 (dd, J=4.7, 1.1 Hz, 1H), 8.02 (d, J=4.8, 2H), 8.10 (d, J=4.7, 2H), 11.80 (s, 1H).

Source