P-Xylene → HCID 11391343, compound

HRID 658446Notes

Reaction equation

HRID 658446 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[OH-].[Na+].CC1C=C[C:19]([CH3:22])=CC=1.C([O-])([O-])=O.[K+].[K+]>O>[CH2:8]([N:9]([CH2:19][CH3:22])[CH2:10][CH2:6][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)[CH3:7]

Participants

6

Reactant 4

HCID 7809P-XyleneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 225235-Nitroindole

Product 1

HCID 11391343HCID 11391343, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A slurry of 5-nitroindole (2.0 g, 12.3 mmol) and NaOH pellets (0.49 g, 1 eq) in H2O (2.0 mL) was stirred at RT. After 10 min, p-xylene (15.0 mL, 1.4 M), K2CO3 (2.55 g, 1.5 equ) and N-diethylaminoethyl chloride hydrochloride (2.12 g, 12.3 mmol, 1 eq) was added, and the reaction mixture was heated to 100° C. After 4 h the reaction mixture was cooled to ambient temperature and concentrated under reduced pressure. The crude residue was dissolved in p-xylene and washed with 1N NaOH (2×) and H2O (1×). The organic layer was dried over MgSO4, filtered, and evaporated under reduced pressure to afford the nitro compound (1.79 g, 56%). TLC (5% MeOH/EtOAc), Rf=0.25; LC MS m/z 262.2 (MH+).

Workup

  1. temperatureAfter 4 h the reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude residue was dissolved in p-xylene
  4. washwashed with 1N NaOH (2×) and H2O (1×)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ef3f62c823b644c480faf06d2ddc0306
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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