Aniline → HCID 9836975, compound

HRID 1595008Notes

Reaction equation

HRID 1595008 reaction equation
[C:1](ON=O)(C)([CH3:3])[CH3:2].C(Br)C=C.[C:12]([C:14]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:15]=1N)#[N:13].NC1C=CC=CC=1>CC#N>[CH2:3]([C:15]1[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:14]=1[C:12]#[N:13])[CH:1]=[CH2:2]

Participants

6

Reactant 4

HCID 6115AnilineHCID 7841Allyl bromideHCID 10906Tert-Butyl nitrite2×HCID 285322-Amino-5-nitrobenzonitrile

Product 1

HCID 9836975HCID 9836975, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °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), 2-cyano-4-nitroaniline (489 mg, 3.0 mmol) was added during 40 minutes, while maintaining the temperature of the reaction mixture at 23-27° 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 26° C. for one hour. The volatile material in the reaction mixture was removed at reduced pressure. Column chromatography (heptane-ethyl acetate 23:2) gave 367 mg (65%) of allyl-2-cyano-4-nitrobenzene as an orange oil. 1H NMR (CDCl3, 400 MHz) δ 8.51, (d, 1H, J=2.4 Hz), 8.39, (dd, 1H, J=8.6, 2.4 Hz), 7.58, (dd, 1H, J=8.6, 0.5 Hz), 6.00-5.90, (m, 1H), 5.29-5.17, (m, 2H), 3.74, (d, 2H, J=6.6 Hz); 13C NMR (CDCl3, 100 MHz) δ 151.3, 146.8, 133.5, 131.4, 128.4,127.9, 119.6, 116.2, 114.4, 38.9; Anal HRMS Calcd. for C10H8N2O2 (M): 188.0585.

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-eb468812b252483892147cb5126ae8b1
Source dataset
uspto-grants-2001_09
Patent number
US06284894B1

Reaction notes

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