2,4-Dimethoxybenzylamine → 4-(2-Chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11128

Reaction equation

HRID 11128 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH:20]2[C:21](=O)[O:22][C:23](=[O:24])[CH:19]2[C:18]2[C:17]3[CH:16]=[C:15]([O:26][CH3:27])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH2:9]1.[CH3:28][O:29][C:30]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:22])[N:33]([CH2:32][C:31]3[CH:34]=[CH:35][C:36]([O:38][CH3:39])=[CH:37][C:30]=3[O:29][CH3:28])[C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:26][CH3:27])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 5972502,4-DimethoxybenzylamineHCID 118435504-(2-Chlorophenyl)-9-methoxy-4,5,6,10c-tetrahydro-1H-furo[3,4-c]carbazole-1,3(3aH)-dione

Product 1

HCID 118430084-(2-Chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of anhydride (286) (2.80 g, 7.42 mmol) prepared as described in example 296 in glacial acetic acid (70 mL) was added 2,4-dimethoxybenzylamine (1.67 mL, 11.1 mmol). The resulting solution was heated at reflux for 6 hours before being partially concentrated under reduced pressure and diluted with water to precipitate an orange solid, which was collected by filtration, washed with water and dried in vacuo. This crude material was then dissolved in p-dioxane and aromatized according to the procedure for example 79, before being chromatographed on silica eluting with ethyl acetate/hexane (1:1). Crystallisation from methanol then gave carbazole (287) (1.46 g, 37%) as a yellow powder, mp 224–226° C. 1H NMR δ [(CD3)2SO] 12.02 (br s, 1H), 8.45 (d, J=2.6 Hz, 1H), 7.62 (s, 1H), 7.58 (m, 2H), 7.53–7.42 (m, 3H), 7.25 (dd, J=8.8, 2.6 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 6.57 (d, J=2.3 Hz, 1H), 6.45 (dd, J=8.4, 2.3 Hz, 1H), 4.68 (s, 2H), 3.88 (s, 3H), 3.80 (s, 3H), 3.72 (s, 3H). Found: C, 68.22; H, 4.37; N, 5.29. C30H23ClN2O5 requires: C, 68.38; H, 4.40; N, 5.32.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 6 hours
  3. concentrationbefore being partially concentrated under reduced pressure
  4. additiondiluted with water
  5. customto precipitate an orange solid, which
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried in vacuo
  9. dissolutionThis crude material was then dissolved in p-dioxane
  10. custombefore being chromatographed on silica eluting with ethyl acetate/hexane (1:1)
  11. customCrystallisation from methanol

Sources & evidence

ORD record
ord-425a6fdd79984f919dc2fb2de7f6baed
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

Loading…