Hydroquinone → HCID 71735772, compound

HRID 1053559Notes

Reaction equation

HRID 1053559 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:11][CH3:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[C:19]1([CH:26]=[CH:25][C:23]([OH:24])=[CH:22][CH:21]=1)[OH:20]>CN(C=O)C>[CH2:11]([N:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][CH2:2][O:20][C:19]1[CH:26]=[CH:25][C:23]([OH:24])=[CH:22][CH:21]=1)[CH3:12]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 7093N-(2-Chloroethyl)-N-ethylanilineHCID 11430Potassium Carbonate

Product 1

HCID 71735772HCID 71735772, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 3a (500 mg, 2.7 mmol), K2CO3 (750 mg, 5.4 mmol), and KI (90 mg, 0.54 mmol) in DMF (50 mL) was bubbled with argon for 10 min Hydroquinone (600 mg, 5.4 mmol) was added to the mixture under argon. The reaction mixture was heated and stirred at 80° C. for 6 hr. The reaction was quenched and the solvent evaporated and purified by silica gel column chromatography to provide compound 3 (400 mg, 1.55 mmol, 57% yield) as a brown oil. 1H NMR (DMSO-d6, 400 MHz) δ 8.92 (s, 1H), 7.14 (m, 2H), 6.75-6.64 (m, 6H), 6.57 (m, 1H), 3.98 (t, J=5.8 Hz, 2H), 3.62 (t, J=5.8 Hz, 2H), 3.41 (q, J=7 Hz, 2H), 1.09 (t, J=7 Hz, 3H). HRMS (ESI, positive) m/z calcd. for C16H20NO2 [M+H]+: 258.1494, found: 258.1436.

Workup

  1. additionwas added to the mixture under argon
  2. temperatureThe reaction mixture was heated
  3. customThe reaction was quenched
  4. customthe solvent evaporated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-2d9be989fcd942bb9ddaa7746fffaf3f
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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