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

HRID 495464Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].CC([O-])(C)C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[NH:65]1[CH2:70][CH2:69][O:68][CH2:67][CH2:66]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[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:65]1[CH2:70][CH2:69][O:68][CH2:67][CH2:66]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 1-bromo-2-methoxy-4-nitro-benzene (2.5 g, 10.8 mmol), Pd2(dba)3 (0.124 g, 0.215 mmol), NaOt-Bu (1.55 g, 16.2 mmol) and BINAP (0.202 g, 0.323 mmol) in toluene (20 mL) at 20° C. was added morpholine (1.5 mL, 17.2 mmol) over 10 min. The mixture was stirred at 80° C. for 3 h when TLC indicated no starting material remained. The mixture was evaporated under reduced pressure followed by the addition of H2O (50 mL). CH2Cl2 extraction (3×15 mL), followed by drying of the combined organic layers with MgSO4 afforded, after filtration and concentration, an orange oil. Chromatography on silica gel (97:3 CH2Cl2/MeOH) yielded pure compound.

Workup

customThe mixture was evaporated under reduced pressure
additionfollowed by the addition of H2O (50 mL)
extractionCH2Cl2 extraction (3×15 mL)
dry with materialby drying of the combined organic layers with MgSO4
customafforded
filtrationafter filtration and concentration
customChromatography on silica gel (97:3 CH2Cl2/MeOH) yielded pure compound

Sources & evidence

ORD record: ord-eee2a55ca773414e9d2350d14d9a359e
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939874B2

Reaction notes

Loading…