4-Hydroxybenzaldehyde → 4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)phenol

Participants

Reaction Steps

To a stirred solution of tryptamine (5.0 g, 31.2 mmole) in dry CH2Cl2 (100 mL) at RT was added 4-hydroxybenzaldehyde (3.81 g, 31.2 mmole) followed by dropwise addition of trifluoroacetic acid (7.11 g, 62.4 mmole). After 12 hr, the reaction solution was washed with 10% aqueous NaHCO3 (100 mL), H2O (100 mL) and brine. The organic solution was dried over Na2SO4 and concentrated under reduced pressure to give a yellow oil. The yellow residue was washed with hexanes and dried under high vacuum to afford the title compound (7.74 g, 94%) as a light yellow solid: MS (ES) m/e 265 (M+H)+.

Provenance & Evidence