Triethyl phosphite → HCID 10108099, compound

Participants

Reaction Steps

1,2,6,7-Tetramethoxy-9H-carbazole/2,3,6,7-Tetramethoxy-9H-carbazole—A stirred solution of 2-((3,4-dimethoxy)phenyl)-4,5,-dimethoxynitrobenzene (6.5 g, 20 mmol) in triethylphosphite (10.5 mL, 6.11 mmol) was heated at 160° C. under a nitrogen atmosphere for 10 hours. The excess triethylphosphite was removed in vacuo, residue was slurried in chloroform the solids were filtered and recrystallized from EtOAc to afford 2,3,6,7-tetramethoxy-9H-carbazole (1.9 g); m.p. 232-233° C. Anal. Calcd. for C16H17NO4: C, 66.88; H, 5.97; N, 4.88. Found: C, 65.04; H, 5.62; N, 4.71. The chloroform filtrate from above was concentrated in vacuo and flash chromatographed (20% EtOAc/CCl4) to afford 1,2,6,7-tetramethoxy-9H-carbazole (1.7 g); m.p. 170-171° C. (MeOH). Anal. Calcd. for C16H17NO4: C, 66.88; H, 5.97; N, 4.88. Found: C, 66.75; H, 5.80; N, 4.88.

Provenance & Evidence