1,2-Dichloro-4-[5-(4-nitrophenyl)-1-pentenyl]benzene → 4-[5-(3,4-Dichlorophenyl)pentyl]phenylamine

HRID 488510Notes

Reaction equation

HRID 488510 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[CH:4][C:3]=1[Cl:22]>[Ni]>[Cl:22][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

3

Reactant 1

HCID 540012121,2-Dichloro-4-[5-(4-nitrophenyl)-1-pentenyl]benzene

Product 1

HCID 222697754-[5-(3,4-Dichlorophenyl)pentyl]phenylamineYield 46%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

The title compound was prepared from 1,2-dichloro-4-[5-(4-nitrophenyl)-1-pentenyl]benzene (2.5 g, 7.4 mmol), Ra—Ni (1 g) in TBF (50 mL) at 25° C. to 40° C. (ΔP=9.9 psi) using the procedure described in Example 1, Step B. This procedure yielded 1.06 g (3.4 mmol, 46%) of the desired product.

Sources & evidence

ORD record
ord-6df64d598b5549fab09c7f66cfe7edf6
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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