Aniline → HCID 9925925, compound

HRID 1595021Notes

Reaction equation

HRID 1595021 reaction equation
[C:1](ON=O)([CH3:4])([CH3:3])[CH3:2].[CH2:8]([Br:11])[CH:9]=C.[N+:12]([C:15]1C=C(C=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)N)([O-:14])=[O:13].NC1C=CC=CC=1>CC#N>[N+:12]([C:15]1[CH:4]=[C:1]([CH2:2][C:8]([Br:11])=[CH2:9])[CH:3]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 6115AnilineHCID 7841Allyl bromideHCID 10906Tert-Butyl nitriteHCID 120683,5-Dinitroaniline

Product 1

HCID 9925925HCID 9925925, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
13 °C

Procedure

To a solution of t-butylnitrite (535 μl, 4.5 mmol) and allyl bromide (3.9 ml, 45.0 mmol) in CH3CN (3 ml), 3,5-dinitroaniline (549 mg, 3.0 mmol) was added during 20 minutes, while maintaining the temperature of the reaction mixture at 11-15° C. At the end of the addition of the aniline extra t-butylnitrite (180 μl, 1.5 mmol) was added to the reaction mixture which then 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 10:1) gave 800 mg (93%) 3,5-dinitro-1-(2-bromo-2-propenyl)benzene as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 8.98, (t, 1H, J=2.1 Hz), 8.47, (d, 2H, J=2.1 Hz), 5.89, (m, 1H), 5.71, (d, 1H, J=2.1 Hz), 4.00, (s, 2H); 13C NMR (CDCl3, 100 MHz) δ 149.05, 142.1, 129.6, 129.3, 121.4, 118.2, 47.3.

Workup

  1. additionwas added to the reaction mixture which
  2. customThe volatile material in the reaction mixture was removed at reduced pressure

Sources & evidence

ORD record
ord-7d9a4409885d4e47a116712be412b0ee
Source dataset
uspto-grants-2001_09
Patent number
US06284894B1

Reaction notes

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