Nitrobenzene → HCID 54354718, compound

HRID 1608929Notes

Reaction equation

HRID 1608929 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[CH2:12]([O:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH3:13].C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC=CC=1)([O-])=O>[Cu]Br.C1(C)C=CC=CC=1.CC(C)=O.N1C=CC=CC=1>[CH2:12]([O:14][C:15]([C:17]1[N:18]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=2)[C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH3:13]

Participants

8

Reactant 4

HCID 7416NitrobenzeneHCID 11430Potassium CarbonateHCID 73125Ethyl indole-2-carboxylateHCID 76114Benzene, 4-bromo-1,2-dimethoxy-

Product 1

HCID 54354718HCID 54354718, compound

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 1049PyridineSolventHCID 20247278Toluene acetoneSolvent

Procedure

4-Bromoveratrole (8.8 g, 40 mmol), indole-2-carboxylic acid ethyl ester (1.9 g, 10 mmol), potassium carbonate (1.9 g), copper- (I) bromide (o.2 g), pyridine (2 ml) and nitrobenzene (10 ml) were stirred at 140° C. for 14 hours. After cooling to room temperature, the reaction mixture was applied onto a silica gel flash chromatography column (silica gel: 140 g). The column was subsequently eluted with toluene (500 ml), toluene/acetone (95:5, 500 ml) and toluene/acetone (90:10, 500 ml). 1-(3,4-Dimethoxyphenyl)indole-2-carboxylic acid ethyl ester was eluted with toluene/acetone (90:10) and gave colorless crystals upon evaporation of the solvent. The crystals were triturated with diisopropyl ether, collected by vacuum filtration and dried in the air. Yield: 3.0 g. (92% of theoretical yield) M.pt.: 126°-128° C. Rf (toluene/acetone, 9:1)=0.53.

Workup

  1. washThe column was subsequently eluted with toluene (500 ml), toluene/acetone (95:5, 500 ml) and toluene/acetone (90:10, 500 ml)
  2. wash1-(3,4-Dimethoxyphenyl)indole-2-carboxylic acid ethyl ester was eluted with toluene/acetone (90:10)
  3. customgave colorless crystals
  4. customupon evaporation of the solvent
  5. customThe crystals were triturated with diisopropyl ether
  6. filtrationcollected by vacuum filtration
  7. customdried in the air
  8. custom(92% of theoretical yield) M.pt.: 126°-128° C

Sources & evidence

ORD record
ord-1bbbc065ab474738a6111ade440e3db4
Source dataset
uspto-grants-1995_03
Patent number
US05399559

Reaction notes

Loading…