Iodine → HCID 11845284, compound

Temperature

50 °C

Into a reactor, equipped with a reflux condenser and under inert gas, 8-fluoro-2H-chromene-5-carboxylic acid amide (4.94 g; 25.6 mmoles), sodium nitrite (4.4 g; 64 mmoles) and isopropyl acetate (40 ml) were charged. The mixture was kept under mechanic stirring and heated at 50° C. In one portion iodine (1.9 g; 7.5 mmoles) and then, in 3 hours, Oxistrong 15® (6 ml) were added. At the end of the addition the reaction mixture was kept under stirring for 1 hour and cooled to 20° C. After addition of water (30 ml), the mixture was further cooled at 5° C. for 1 hour. The solid was filtered and washed with isopropyl acetate (3×10 ml), pre-cooled at 0° C., and with water (2×10 ml). After drying in oven under vacuum at 50° C. overnight, 8-fluoro-3-nitro-2H-chromene-5-carboxylic acid amide (4.7 g; HPLC titre 90%; 70% yield) was obtained. The mother liquors of the reaction were treated with a 15% solution of sodium metabisulphite (20 ml) up to decoloration. The phases were separated, the organic phase was dried and the organic solvent was removed under reduced pressure obtaining a solid (0.8 g) containing 49% of 8-fluoro-3-nitro-2H-chromene-5-carboxylic acid amide. Overall yield: 76.4%.

1. additionwere charged
2. additionOxistrong 15® (6 ml) were added
3. additionAt the end of the addition the reaction mixture
4. stirringunder stirring for 1 hour
5. temperaturecooled to 20° C
6. temperaturethe mixture was further cooled at 5° C. for 1 hour
7. filtrationThe solid was filtered
8. washwashed with isopropyl acetate (3×10 ml)
9. temperaturepre-cooled at 0° C.
10. customAfter drying in oven under vacuum at 50° C. overnight

ORD record

ord-6391f7664d7b48b8a7c86530a1282a91

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07265251B2