Borane → HCID 22726863, compound

To a suspension of 3-mercaptoisonicotinic acid (1.80 g, 11.6 mmol) in dry THF (70 mL) was added slowly borane in THF (52 mL, 1 M, 52 mmol) and the reaction mixture was stirred for 30 min. The solvent was evaporated under reduced pressure, methanol (40 mL) was added, and after gas evolution stopped, concentrated hydrochloric acid (3.6 mL) was added. The solution was filtered and the filtrate was evaporated to dryness. The residue was redissolved in a small volume of water, concentrated aqueous ammonia (3.6 mL) was added and the reaction mixture was evaporated to dryness. After overnight drying under vacuum, a quantitative yield of the title product was obtained, which was used for the next step without purification. 1H NMR (CD3OD) δ 4.78 (s, 2H), 8.13 (d, 2H, J=6), 8.60 (d, 2H, J=6), 8.70 (s, 1H).

1. customThe solvent was evaporated under reduced pressure, methanol (40 mL)
2. additionwas added
3. additionconcentrated hydrochloric acid (3.6 mL) was added
4. filtrationThe solution was filtered
5. customthe filtrate was evaporated to dryness
6. dissolutionThe residue was redissolved in a small volume of water, concentrated aqueous ammonia (3.6 mL)
7. additionwas added
8. customthe reaction mixture was evaporated to dryness
9. customAfter overnight drying under vacuum

ORD record

ord-12e1b68f5ed0434ebf27a2da2fed72b6

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06723716B1