Triethyl phosphite → HCID 10108099, compound

HRID 636652Notes

Reaction equation

HRID 636652 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[N+:21]([O-])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(OP(OCC)OCC)C>>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[C:11]3[C:12](=[CH:13][C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=3)[NH:21][C:6]=2[CH:7]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 10041613HCID 10041613, compound

Product 1

HCID 10108099HCID 10108099, compoundYield 33.1%

Procedure

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.

Workup

  1. customThe excess triethylphosphite was removed in vacuo, residue
  2. filtrationwere filtered
  3. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-dcee58b78faa4552a2833da9b04b52a9
Source dataset
uspto-grants-2001_02
Patent number
US06194439B1

Reaction notes

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