Hydrochloric Acid → HCID 10888757, compound

Participants

Reaction Steps

A solution of 2 (1.75 g, 7.5 mmol) in a mixture of methanol (100 mL), water (20 mL) and conc. HCl (10 mL) was refluxed for 4 h. The solution was diluted with water (30 mL), concentrated to about 50 mL, basified to pH 8 with K2CO3 and extracted with EtOAc. The combined organic phases were washed with brine, dried and evaporated to give methyl indoline-5-acetate 3 as a brown oil (1.06 g, 74%); 1H NMR: δH (90 MHz) 6.80-7.06 (m, 2H), 6.58 (d, J=8 Hz, 1H), 3.64 (s, 3H), 3.52 (t, J=7.2 Hz, 3H), 3.50 (s, 2H) and 2.96 (t, J=7.2 Hz, 2H). The crude product and glutaric anhydride (685 mg, 6 mmol) were dissolved in chloroform (75 mL) and the mixture was stirred at rt overnight, then refluxed for 2 h. The solution was extracted with saturated aq. NaHCO3 solution and the aqueous extract was acidified to pH 2.8 with conc. HCl and extracted with EtOAc. The latter organic extracts were dried and evaporated to give 4 as white crystals (1.24 g, 74%), mp 134-136° C. (EtOAc-hexanes); IR: νmax/cm−1; 1720, 1.625, 1605; 1H NMR: δH (400 MHz) 8.15 (d, J=8 Hz, 1H), 7.07-7.11 (m, 2H), 4.04 (t, J=8.5 Hz, 2H), 3.68 (s, 3H), 3.57 (s, 2H), 3.18 (t, J=8.5 Hz, 2H), 2.52 (t, J=7 Hz, 4H), and 2.06 (quintet, J=7 Hz, 2H). Anal. Calcd for C16H19NO5: C, 56.11; H, 5.07; N,. 10.06. Found: C, 56.18; H, 4.86; N, 10.03.

Provenance & Evidence