Sulfuric Acid → HCID 22247299, compound

Participants

Reaction Steps

0.88 (3H, br-t, J=7 Hz, —(CH2)7CH3), 1.00˜1.70 (121H, m, —H2(CH2)f—), 2.47 (3H, s, indoline C6—CH3), 3.02 (2H, t, J=8 Hz, indoline C3—H2), 3.03 (2H, t, J=7 Hz, >NCH2—), 3.69 (2H, t, J=8 Hz, indoline C2—H2), 5.00 (IH, br, -2H), 7.73 (1H, s, indoline C4—H). (4) 1-Octyl-5-carboxy-6-methyl-7-nitroindoline (1.4 g) was dissolved in methanol (30 ml), and conc. sulfuric acid (4.1 g) was added, which was followed by refluxing for 4 hr. Methanol was evaporated under reduced pressure. Ethyl acetate (100 ml) was added to the residue. The mixture was washed with water and dried over anhydrous sodium sulfate. Ethyl acetate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/ methanol=1/10−10/1) to give 750 mg of 1-octyl-5-methoxycarbonyl-6-methyl-7-nitroindoline as crystals.

Provenance & Evidence