Hydrochloric Acid → HCID 66616399, compound

Participants

Reaction Steps

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.

Provenance & Evidence