Phosphorus trichloride → N-(4-Methoxybenzyl)-4-nitropyridin-2-amine

HRID 1894969Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a 2 L 3 neck round bottom flask fitted with a mechanical stirrer, was added N-(4-methoxybenzyl)-4-nitropyridin-2-amine 1-oxide (38.72 g, 0.14 mol) and chloroform (580 mL). The reaction mixture was cooled to 0° C. and phosphorus trichloride (36.8 mL, 0.42 mol) was added dropwise. The reaction mixture was allowed to warm to rt and stir overnight. The reaction mixture was filtered and the resulting solid was slurried with hexanes and filtered (repeated several times) to afford N-(4-methoxybenzyl)-4-nitropyridin-2-amine (39.34 g, 102%) as a yellow solid. LCMS: (FA) ES+ 260; 1H NMR (400 MHz, CD3OD) δ ppm 8.20 (d, J=5.9 Hz, 1H), 7.33-7.25 (m, 1H), 7.22 (dd, J=5.9, 2.0 Hz, 1H), 6.89 (d, J=8.7 Hz, 1H), 4.51 (s, 1H), 3.77 (s, 1H).

Workup

temperatureto warm to rt
filtrationThe reaction mixture was filtered
filtrationfiltered (repeated several times)

Sources & evidence

ORD record: ord-356cc83a846f40d9a85b38ddd6b2f79d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513421B2

Reaction notes

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