Methanol → 4-[3-(Ethyloxy)-4-nitrophenyl]-1-propylpyridinium acetate

HRID 419514Notes

Reaction equation

[Cl-].[N+]([C:5]1[CH:10]=C([N+]([O-])=O)C=C[C:6]=1[N+:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([O:29][CH2:30][CH3:31])[CH:21]=2)=[CH:16][CH:15]=1)([O-])=O.C(N)CC.C[OH:37]>CC(C)=O>[C:30]([O-:37])(=[O:29])[CH3:31].[CH2:30]([O:29][C:22]1[CH:21]=[C:20]([C:17]2[CH:16]=[CH:15][N+:14]([CH2:6][CH2:5][CH3:10])=[CH:19][CH:18]=2)[CH:25]=[CH:24][C:23]=1[N+:26]([O-:28])=[O:27])[CH3:31]

Participants

Conditions

Temperature: 100 °C

Procedure

To 1-(2,4-dinitrophenyl)-4-[3-(ethyloxy)-4-nitrophenyl]pyridinium chloride (1.2 g, 2.57 mmol) in 10 mL of MeOH was added, propylamine (0.151 g, 2.57 mmol). The mixture was heated to 100° C. for 4 h. The mixture was cooled and rotovaped down. The product was taken up in acetone. This solution was loaded onto a short silica gel column and eluted with EtOAc (˜500 mL) to remove the aniline by product. The product was then eluted with 300 mL of (10% HOAc/10% MeOH/80% DCM). The solvent was rotovaped down to give the title compound of step C (0.84 g, 2.42 mmol, 94%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.23 (d, J=6.96 Hz, 2H), 8.63 (d, J=6.96 Hz, 2H), 8.07 (d, J=8.42 Hz, 1H), 7.90 (d, J=1.65 Hz, 1H), 7.74 (dd, J=8.42, 1.83 Hz, 1H), 4.59 (t, J=7.23 Hz, 2H), 4.38 (q, J=7.08 Hz, 2H), 1.91-2.00 (m, 2H), 1.86 (s, 3H), 1.35 (t, J=6.96 Hz, 3H), 0.89 (t, J=7.33 Hz, 3H).

Workup

temperatureThe mixture was cooled
washeluted with EtOAc (˜500 mL)
customto remove the aniline by product
washThe product was then eluted with 300 mL of (10% HOAc/10% MeOH/80% DCM)

Sources & evidence

ORD record: ord-ed259cba53ae4f8884f837df977fbc51
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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