Reaction #3125538
Related Literature (1)
openreactiondata ↗doi:10.6084/m9.figshare.5104873.v1; patent:US04740511
Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of methyl 2-phenylaminonicotinate (5 g.), gamma-octanoic lactone (10 g.) and potassium t-butoxide (7.5 g.) was stirred in a nitrogen atmosphere and heated to 95° C. where it was held for 6 hrs. After cooling, the mixture was poured into 5% NaOH (200 ml.) and stirred overnight. Acidification to pH 4.6 yielded an oil, which was extracted with ether, washed with water, dried (Na2SO4), filtered, and evaporated to a small volume. Hexane was added until turbidity was noticed, and the mixture was allowed to stand for about 5 hrs. The solid was filtered off and recrystallized from CH2Cl2 /isopropanol/isopropyl ether to produce the desired product, m.p. 184°-186° C. After cooling stirred overnight Acidification to pH 4.6 yielded an oil, which was extracted with ether washed with water dried (Na2SO4) filtered evaporated to a small volume Hexane was added until turbidity to stand for about 5 hrs The solid was filtered off recrystallized from CH2Cl2 /isopropanol/isopropyl ether
Source ID: ord-80b97ae324f84030b41ae1a9de5541b5