Indoline → HCID 22247323, compound

Participants

Reaction Conditions

Reaction Steps

0.87 (3H, br-t, J=7 Hz, —(CH2)7CH3), 1.00-1.70 (12H, m, —CH2(CH2)6—), 1.34 (9H, s, —C(CH3)3), 2.39 (3H, s, indoline C6—CH3), 2.93 (2H, t, J=8 Hz, indoline C3—H2), 3.25 (2H, t, J=7 Hz, >NCH2—), 3.51 (2H, t, J=8 Hz, indoline C2—H2), 3.79 (3H, s, —CO2 CH3), 6.76 (1H, br, —CONH—), 7.55 (1H, s, indoline Ce—H). (6) N-(1-Octyl-5-methoxycarbonyl-6-methylindolin-7-yl)-2,2-dimethylpropanamide (580 mg) was dissolved in methanol (10 ml) and a solution of NaOH (290 mg) in water (5 ml) was added, which was followed by stirring at 60° C. for 4 hr. Methanol was evaporated under reduced pressure. Water (50 ml) was added to the residue and the mixture was washed with ethyl acetate (20 ml). The aqueous layer was adjusted to pH 6-7 with 2N sulfuric acid and extracted with chloroform (100 ml). The chloroform layer was washed with water and dried over anhydrous sodium. sulfate. Chloroform was evaporated under reduced pressure to give 380 mg of the title compound.

Provenance & Evidence