Isobutanol → HCID 67186669, compound

Temperature

80 °C

Sodium metal (7.3 g, 0.32 mol) was added in small portions to 2-methyl-1-propanol (145 mL, 0.63 mol) at 80° C. over 30 min period, and the reaction mixture was stirred for an additional 3 h at 80° C. Subsequently, a solution of commercially available 3-chloroisonicotinic acid (10 g, 63 mmol) in 5 mL of DMSO was added to the reaction mixture at 80° C. The resulting slurry was heated to 120° C. for an additional 16 h, then cooled down to room temperature, concentrated down to half volume under the reduced pressure, and filtered. The filtrate was concentrated down to half volume under the reduced pressure, and filtered again. The combined solids were mixed with 10 mL of MeOH and 1 mL of water and acidified with concentrated HCl at 0° C. to pH=7. The resulting precipitate was filtered out and dried under vacuum, resulting in 10 g (81%) of 3-isobutoxyisonicotinic acid. 1H-NMR (400 MHz, d6-DMSO): δ 8.47 (s, 1H), 8.23 (d, 1H), 7.46 (d, 1H), 3.91 (d, 2H), 2.04 (m, 1H), 0.94 (d, 6H). MS (EI) for C10H13NO3: 196 (MH+).

1. temperatureThe resulting slurry was heated to 120° C. for an additional 16 h
2. temperaturecooled down to room temperature
3. concentrationconcentrated down to half volume under the reduced pressure
4. filtrationfiltered
5. concentrationThe filtrate was concentrated down to half volume under the reduced pressure
6. filtrationfiltered again
7. additionThe combined solids were mixed with 10 mL of MeOH and 1 mL of water
8. customacidified with concentrated HCl at 0° C. to pH=7
9. filtrationThe resulting precipitate was filtered out
10. customdried under vacuum
11. customresulting in 10 g (81%) of 3-isobutoxyisonicotinic acid

ORD record

ord-ab62a693f1f34c48b06d1b013b9a0d7e

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324231B2