4-[5-(3,4-Dichlorophenyl)pentyl]phenylamine → 2-{4-[5-(3,4-Dichlorophenyl)-pentyl]phenylamino}4-methoxy-5-nitrobenzoic acid methyl ester

HRID 488512Notes

Reaction equation

HRID 488512 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:21][O:22][C:23](=[O:36])[C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[C:27]([O:33][CH3:34])=[CH:26][C:25]=1F>C1COCC1>[CH3:21][O:22][C:23](=[O:36])[C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[C:27]([O:33][CH3:34])=[CH:26][C:25]=1[NH:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 222697754-[5-(3,4-Dichlorophenyl)pentyl]phenylamineHCID 23404649Methyl 2-fluoro-4-methoxy-5-nitrobenzoate

Product 1

HCID 540571152-{4-[5-(3,4-Dichlorophenyl)-pentyl]phenylamino}4-methoxy-5-nitrobenzoic acid methyl esterYield 37.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared from 4-[5-(3,4-dichlorophenyl)pentyl]phenylamine (231 mg, 0.75 mmol), LHDMS (6.28 mL, 1 M in THF, 6.28 mmol) and 2-fluoro-4-methoxy-5-nitrobenzoic acid methyl ester (172 g, 0.75 mmol) in THF (5 mL) using the procedure described in Example 13. Purification by flash chromatography (silica gel, 10% EtOAc/hexane) yielded 145 mg (0.28 mmol, 37%) of the desired product

Workup

  1. customPurification by flash chromatography (silica gel, 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-173e5b01c236409f818c9d6d5c41dafa
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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