Morpholine → 4-(2-Methoxy-4-nitrophenyl)morpholine

HRID 2091961Notes

Reaction equation

HRID 2091961 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C(OCC)(=O)C>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 705192-Chloro-5-nitroanisole

Product 1

HCID 219364654-(2-Methoxy-4-nitrophenyl)morpholineYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A pressure bottle was charged with 1-chloro-2-methoxy-4-nitrobenzene (10.0 g mg, 53.3 mmol, purchased from TCI America) and morpholine (15 mL, 172.0 mmol). The reaction mixture was stirred at 120° C. for 15 hours and it was allowed to cool to room temperature by itself. The resulting solid was suspended in 20 mL of ethyl acetate, filtered, and washed with 20 mL of tert-butyl methyl ether. 8.8 g of yellow solid as the desired product AA was collected (69% yield). 1H-NMR (400 MHz, d6-DMSO): 7.83 (dd, 1H), 7.67 (d, 1H), 6.98 (d, 1H), 3.88 (s, 3H), 3.71 (m, 4H), 3.16 (m, 4H). MS (EI) CH11H14N2O4: 239 (M+H)+.

Workup

  1. temperatureto cool to room temperature by itself
  2. filtrationfiltered
  3. washwashed with 20 mL of tert-butyl methyl ether
  4. custom8.8 g of yellow solid as the desired product AA was collected (69% yield)

Sources & evidence

ORD record
ord-5d9e95430c4f4464b2ef8f4bd0d60768
Source dataset
uspto-grants-2013_05
Patent number
US08440663B2

Reaction notes

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