Aniline → HCID 9817275, compound

HRID 1595020Notes

Reaction equation

C(ON=O)(C)(C)C.[C:8]1([C:14]([CH2:16]Br)=[CH2:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N+:18]([C:21]1[CH:22]=[C:23]([CH:25]=[C:26]([N+:28]([O-:30])=[O:29])[CH:27]=1)N)([O-:20])=[O:19].NC1C=CC=CC=1>CC#N>[N+:18]([C:21]1[CH:22]=[C:23]([CH2:16][C:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH2:15])[CH:25]=[C:26]([N+:28]([O-:30])=[O:29])[CH:27]=1)([O-:20])=[O:19]

Participants

Conditions

Temperature: 25.5 °C

Procedure

To a solution of t-butylnitrite (119 μl, 1.0 mmol) and 2-phenyl-3-brompropene (0.99 g, 5.0 mmol) in CH3CN (0.5 ml) was 3,5-dinitroaniline (92 mg, 0.5 mmol) added during 10 minutes, while maintaining the temperature of the reaction mixture at 23-28° C. At the end of the addition of the aniline extra t-butylnitrite (119 μl, 1.0 mmol) was added to the reaction mixture which then was heated to 35° C. for 5 minutes. The reaction mixture was stirred at 22° C. for one hour. The volatile material in the reaction mixture was removed at reduced pressure. Column chromatography (heptane-ethyl acetate 23:2) succeeded by crystallization from heptane gave 50 mg (35%) of 3,5-dinitro-1-(2-phenyl-2-propenyl)benzene as bright yellow needles. 1H NMR (CDCl3, 400 MHz) δ 8.88, (t, 1H, J=2.1 Hz), 8.42, (d, 2H, J=2.1 Hz), 7.42-7.37, (m, 2H), 7.36-7.24, (m, 3H), 5.65, (s, 1H), 5.22, (d, 1H, J=0.8 Hz), 4.08, (s, 2H).

Workup

additionadded during 10 minutes
additionwas added to the reaction mixture which
temperaturethen was heated to 35° C. for 5 minutes
customThe volatile material in the reaction mixture was removed at reduced pressure
customColumn chromatography (heptane-ethyl acetate 23:2) succeeded by crystallization from heptane

Sources & evidence

ORD record: ord-9d3c3deffd4a434a81942aedfc1b0645
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06284894B1

Reaction notes

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