Morpholine → N-(2-methoxy-4-morpholino-6-nitrophenyl)acetamide

HRID 1188777Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([NH:11][C:12](=[O:14])[CH3:13])=[C:4]([O:15][CH3:16])[CH:3]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.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.CC([O-])(C)C.[K+]>O1CCOCC1>[CH3:16][O:15][C:4]1[CH:3]=[C:2]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]=1[NH:11][C:12](=[O:14])[CH3:13]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of N-(4-bromo-2-methoxy-6-nitrophenyl)acetamide (2.89 g), morpholine (2.61 g), BINAP (1.21 g) and t-BuOK (1.53 g) in dioxane (50 mL) was degassed with N2 and the mixture was stirred at 110° C. in a sealed tube overnight. It was cooled to room temperature and filtered. The filtrate was concentrated in-vacuo. The residue was purified by silica gel chromatography eluted with MeOH/DCM=1/50 to afford the desired product (1.03 g, 35%) 1H NMR (300 MHz, CDCl3) δ ppm 2.15 (s, 1H), 3.18 (t, 4H, J=4.8 Hz), 3.85 (t, 4H, J=4.8 Hz), 3.88 (s, 3H), 6.63 (d, 1H, J=2.7 Hz), 6.96 (d, 1H, J=2.7 Hz).

Workup

customwas degassed with N2
temperatureIt was cooled to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated in-vacuo
customThe residue was purified by silica gel chromatography
washeluted with MeOH/DCM=1/50

Sources & evidence

ORD record: ord-2b047dfcb13f4d1db4d29387ac536853
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674090B2

Reaction notes

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