Aniline → 2-Allyl-5-nitrobenzophenone

HRID 1595011Notes

Reaction equation

HRID 1595011 reaction equation
[C:1](ON=O)(C)([CH3:3])[CH3:2].C(Br)C=C.N[C:13]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:14]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].NC1C=CC=CC=1>CC#N>[CH2:3]([C:13]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:14]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16])[CH:1]=[CH2:2]

Participants

6

Reactant 4

HCID 6115AnilineHCID 7841Allyl bromideHCID 10906Tert-Butyl nitrite2×HCID 156812-Amino-5-nitrobenzophenone

Product 1

HCID 98168012-Allyl-5-nitrobenzophenoneYield 46.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °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-amino-5-nitrobenzophenone (727 mg, 3.0 mmol) was added during 20 minutes while maintaining the temperature of the reaction mixture at 28-32° C. At the end of the addition of the aniline, extra t-butylnitrite (360 μl, 3 mmol) was added to the reaction mixture which then was stirred at 25° C. for one hour. The volatile material in the reaction mixture was removed at reduced pressure. Column chromatography (heptane-ethyl acetate 23:2) gave 370 mg (46%) of 2-allyl-5-nitrobenzophenone as a light yellow oil. 1H NMR (CDCl3, 300 MHz) δ 8.29, (dd, 1H, J=8.6, 2.5 Hz), 8.18, (d, 1H, J=2.4 Hz), 7.81-7.74, (m, 2H), 7.69-7.60, (m, 1H), 7.57-7.45, (m, 3H), 5.93-5.88, (m, 1H), 5.09-5.95, (m, 2H), 3.53, (m, 2H, J=6.6 Hz).

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-26710dfdb70748e7b2ebf5cd0910e1c8
Source dataset
uspto-grants-2001_09
Patent number
US06284894B1

Reaction notes

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