The femtosecond internal conversion (IC) of the tryptophan sidechain analog 5-methoxyindole (5MI) in hexadecane (HD) was observed using fluorescence upconversion. The time constant for internal conversion between L-1(a), and L-1(b) was estimated at 10-40 fs. A triple-exponential emission anisotropy decay, due to molecular reorientation, was also observed. The dependence of initial anisotropy upon excitation wavelength sets limits on L-1(a) vs. L-1(b) transition oscillator orientations.