Methanol → 4-[4-(3,4-Dichlorophenyl)butyl]phenylamine

HRID 488505Notes

Reaction equation

HRID 488505 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[CH:4][C:3]=1[Cl:21].CO>C1COCC1.[Ni]>[Cl:21][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 887MethanolHCID 86594892(trans)-1,2-Dichloro-4-[4-(4-nitrophenyl)-1,3-butadienyl]benzene

Product 1

HCID 136560814-[4-(3,4-Dichlorophenyl)butyl]phenylamineYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from (trans), (trans)-1,2-dichloro-4-[4-(4-nitrophenyl)-1,3-butadienyl]benzene (15.42 g, 0.048 mol), Ra—Ni (1 g) at 20° C. to 26° C. (ΔP=19.3 psi) under a hydrogen atmosphere in THF (75 mL) and MeOH (75 mL) using the procedure described in Example 1, Step B. This procedure yield a solid, 10.97 g (0.037 mol, 78%) of the desired product. mp 50-52° C.

Sources & evidence

ORD record
ord-957fff5b326f4687a42a0a00df8bda8c
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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