Triethylamine → HCID 178430904, compound

Participants

Reaction Conditions

Reaction Steps

Et3N (300 μL, 2.152 mmol) and (PhO)2PON3 (440 μL, 2.064 mmol) were added to a C6H6 (10.0 mL) suspension of 3-(4-methylpyrazol-5-yl)-2-naphthoic acid (Preparation 10) (257 mg, 1.019 mmol), and the mixture was heated at 50° C. for 2 hr. The volatile component was removed in vacuo, and the resulting yellow solid was dissolved in o-dichlorobenzene (8.0 mL) and heated at 150° C. for 4 hr. During the latter heating, there was a gradual evolution of gas accompanied by the formation of a suspension. The reaction mixture was allowed to cool to RT, and the precipitate was filtered and washed with copious ether to afford the title compound as a fluffy light-yellow solid (170.8 mg, 67%). 1H NMR (DMSO, δ=2.50): 11.86 (s, 1H), 8.57 (s, 1H), 8.13 (d, J=8.2, 1H), 7.99 (s, 1H), 7.92 (d, J=8.3, 1H), 7.22 (s, 1H), 7.56 (app t, J=7.21, 1H), 7.49 (app t, J=7.48, 1H), 2.60 (s, 3H). (ESI) m/z (M+H)+=250.00.

Provenance & Evidence