1-Fluoro-2-nitrobenzene → HCID 23353522, compound

HRID 235129Notes

Reaction equation

HRID 235129 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.F[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27].C(OCC)(=O)C.CCOCC>CN(C)C1C=CN=CC=1.CN(C=O)C>[N+:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)([O-:28])=[O:27]

Participants

6

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 21584169Diethylether ethylacetateHCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 23353522HCID 23353522, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

The title product was obtained following the procedure of example 27 by reacting 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.225 g, 0.93 mmol), 2-fluoronitrobenzene (0.255 g, 1.8 mmol), and 4-dimethylaminopyridine (0.167 g, 1.37 mmol) in dry DMF (5 mL) with an overnight reflux. The product was isolated by silica gel flash chromatography and recrystallization from ethyl acetate/ether to yield 0.024 g (7%) of the title compound as orange crystals: mp 87°-94° C.; 1H NMR δ 9.70 (br s, 1H), 8.26 (dd, J=1.5, 8.5 Hz, 1H), 8.07 (d, J=2 Hz, 1H), 7.87 (d, J=8.5 Hz, 1H), 7.57 (s, J=8 Hz, 1H), 7.44-7.32 9m, 4H), 7.16 (dd, J=1,7.5 Hz, 1H), 6.82 (dd, J=6.5, 8.5 Hz, 1H), 3.15 (br s, 4H), 2.70 (br s, 4H), 2.41 (s, 3H). HRMS m/e calculated for C21H22N4O2 ; 362.1738. Observed m/e: 362.1736.

Workup

  1. customwith an overnight
  2. temperaturereflux

Sources & evidence

ORD record
ord-3c14bc835c744adaa315923d0f81999c
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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