Hydrochloric Acid → HCID 66616399, compound

To 5-chloro-N1,N3-diisobutylisophthalamide (8.1 g, 26.1 mmol) was added borane (1 M solution in THF, 130.0 mL, 130.0 mmol). The reaction mixture was stirred at rt under nitrogen for 32 h. The starting material was still remaining. Additional borane (50 mL of 1 M solution in THF) was added and the reaction mixture was heated at 60° C. for another 6 h, then cooled to rt. To the mixture were added 100 mL of MeOH and HCl solution (100 mL of 4 N HCL) were added and the mixture was stirred for 2 h. The resulting mixture was concentrated in vacuo. The residue was diluted with ethyl acetate and water. The pH of the aqueous layer was adjusted ro pH 9 using act NaOH. It was mixed with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated to give the product as a colorless oil (6.0 g, 72%). 1H NMR (CD3OD): δ 7.31 (s, 2H), 7.26 (s, 1H), 3.76 (s, 4H), 2.39 (d, J=6.8 Hz, 4H), 1.80 (m, 2H), 0.94 (d, J=6.8 Hz, 12H); MS (ESI): (M+H)+=283.4.

1. temperaturethe reaction mixture was heated at 60° C. for another 6 h
2. temperaturecooled to rt
3. additionwere added
4. stirringthe mixture was stirred for 2 h
5. concentrationThe resulting mixture was concentrated in vacuo
6. additionThe residue was diluted with ethyl acetate and water
7. additionIt was mixed with ethyl acetate
8. washThe organic layer was washed with brine
9. dry with materialdried over MgSO4
10. concentrationconcentrated

ORD record

ord-d1a0c456e8d24c52b98eb340c165b10b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501992B2