p-Fluoronitrobenzene → 5,6-Dimethoxy-1-(4-nitrophenyl)-indoline

HRID 1582501Notes

Reaction equation

HRID 1582501 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[NH:18][CH2:17][CH2:16]2.C(=O)([O-])O.[Na+]>CS(C)=O>[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[O:22][CH3:23])[N:18]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 516892Sodium BicarbonateHCID 110629785,6-Dimethoxyindoline

Product 1

HCID 227173945,6-Dimethoxy-1-(4-nitrophenyl)-indolineYield 65.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6.3 g of 4-nitrofluorobenzene (0.045 mol) were stirred with 8.0 g of 5,6-dimethoxyindoline (0.045 mol) and 4.2 g of sodium hydrogen carbonate (0.050 mol) for 2.5 h at 80° C. in 50 ml of DMSO. After cooling, the mixture was poured onto ice, the precipitate was removed by filtration under suction and the product was dried in vacuo at 45° C. The intermediate product 5,6-dimethoxy-1-(4-nitrophenyl)-indoline was obtained in a yield of 65.6% (melting point: 176-179° C.).

Workup

  1. temperatureAfter cooling
  2. additionthe mixture was poured onto ice
  3. customthe precipitate was removed by filtration under suction
  4. customthe product was dried in vacuo at 45° C

Sources & evidence

ORD record
ord-09237c26c15543bc99c681aae604be52
Source dataset
uspto-grants-2004_05
Patent number
US06736862B2

Reaction notes

Loading…