Hydroquinone → HCID 59452668, compound

HRID 419461Notes

Reaction equation

HRID 419461 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[CH2:10])[CH:6]=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C1(C=CC(O)=CC=1)O>CC(O)C>[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:10][CH2:9][C:7]2[CH:6]=[CH:5][C:4]([N+:11]([O-:13])=[O:12])=[C:3]([O:2][CH3:1])[CH:8]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 531671-MethylpiperazineHCID 536287222-Methoxy-1-nitro-4-vinylbenzene

Product 1

HCID 59452668HCID 59452668, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To 5-ethenyl-2-nitrophenyl methyl ether (0.55 g, 3.1 mmol) in 10 mL of iPrOH was added, 1-methylpiperazine (0.614 g, 6.13 mmol), and catalytic hydroquinone (0.033 g, 0.31 mmol). The mixture was heated to 90° C. for 18 h. The solvent was rotovaped down and the crude product was purified by flash chromatography to give the title compound of step C (0.6 g, 2.15 mmol, 70%). 1H NMR (400 MHz, CDCl3) δ ppm 7.79 (d, J=8.24 Hz, 1H), 6.93 (s, 1H), 6.84 (dd, J=8.33, 1.19 Hz, 1H), 3.93 (s, 3H), 2.79-2.89 (m, 2H), 2.40-2.69 (m, 10H), 2.29 (s, 3H).

Workup

  1. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-37f3997fe79f4c9d92e5e4399fd3504e
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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