Hydroquinone → HCID 18469783, compound

HRID 2228373Notes

Reaction equation

HRID 2228373 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.[C:16]([O-:21])(=[O:20])[C:17]([CH3:19])=[CH2:18].[K+].[I-].[K+].CNC=O.C1(C=CC(O)=CC=1)O>>[C:16]([O:21][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)(=[O:20])[C:17]([CH3:19])=[CH2:18]

Participants

6

Reactant 5

HCID 785HydroquinoneHCID 4875Potassium IodideHCID 31254N-MethylformamideHCID 18469781HCID 18469781, compoundHCID 23667354Potassium methacrylate

Product 1

HCID 18469783HCID 18469783, compoundYield 92.3%

Procedure

Next, into a flask of 200 ml capacity fitted with a stirrer and cooling tube, there were introduced 14.9 g of 1-(2-chloroethyl)-4-nitroindole, 18.0 g of potassium methacrylate, 6.0 g of potassium iodide, 40 ml of N, N-methyl formamide and a small quantity of hydroquinone, these then being heated to 100° C., and stirred for 2.5 hours. After the reaction had been completed, insoluble material was removed by filtration, and concentration was performed under reduced pressure. Furthermore, this reaction mixture was purified by column chromatography using silica gel, to obtain 16.8 g of 1-(2-methacryloyloxyethyl)-4-nitroindole.

Workup

  1. customNext, into a flask of 200 ml capacity fitted with a stirrer
  2. temperaturecooling tube
  3. custominsoluble material was removed by filtration, and concentration
  4. customFurthermore, this reaction mixture was purified by column chromatography

Sources & evidence

ORD record
ord-882e645a037d43899eac45eb1b200b14
Source dataset
uspto-grants-2002_07
Patent number
US06416939B1

Reaction notes

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