Trifluoroacetic acid → HCID 131717951, compound

Temperature

125 °C

A mixture of 4 g (28.96 mmol) of 5-aminonicotinic acid, 35 ml Ac2O, and 2 ml CF3CO2H in a stainless steel bomb was heated 22 hr at 125° C. (oil bath temperature). The reaction mixture was evaporated to dryness at 55° C./20 mm pressure and 55° C./1 mm pressure. The gummy residues were mixed with methanol and again evaporated to dryness. The residues were mixed with 50 ml concentrated NH4OH, allowed to stand about 2 hr at room temperature, and evaporated to dryness at 60° C. under reduced pressure. The residues were mixed with 25 ml ethanol and again evaporated to dryness. The residue afforded a light beige crystalline material upon trituration with warm ethanol. The solid product was collected and dried to afford 4.55 g (80% yield) of 5-acetamidonicotinic acid, ammonium salt.

1. customThe reaction mixture was evaporated to dryness at 55° C./20 mm pressure and 55° C./1 mm pressure
2. additionThe gummy residues were mixed with methanol
3. customagain evaporated to dryness
4. additionThe residues were mixed with 50 ml concentrated NH4OH
5. customevaporated to dryness at 60° C. under reduced pressure
6. additionThe residues were mixed with 25 ml ethanol
7. customagain evaporated to dryness
8. customThe residue afforded a light beige crystalline material upon trituration with warm ethanol
9. customThe solid product was collected
10. customdried

ORD record

ord-20b1e768b18d400a989a799efc08204f

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05215738