Reaction #2439954

Reaction equation

N-[4-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide

N-(4-aminophenyl)morpholine

→

title compound

Yield 48.4%

N-(4-{3-[(4-Morpholin-4-yl-phenylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-5-carbonyl}-phenyl)-acetamide

Yield 48.4%

Solvents

THF

—

Hexanes

Conditions

Workup

1. 1
   OtherA small screw cap test tube
2. 2
   TemperatureSubsequently, the reaction mixture was cooled to room temperature
3. 3
   OtherThe solid precipitate that formed

Procedure

A small screw cap test tube was charged with N-[4-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide (prepared below, 50 mg, 0.155 mmol) and THF (2 mL). To the resulting solution was added N-(4-aminophenyl)morpholine (30.4 mg, 0.170 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture. The solid precipitate that formed was washed with ˜1 mL of i-prOH yielding 41% (31 mg, 0.075 mmol) of the title compound.

Source