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

HRID 488499Notes

Reaction equation

HRID 488499 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:19][O:20][C:21](=[O:34])[C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25]([O:31][CH3:32])=[CH:24][C:23]=1F.CCN(CC)CC>CC#N.C(Cl)Cl>[CH3:19][O:20][C:21](=[O:34])[C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[C:25]([O:31][CH3:32])=[CH:24][C:23]=1[NH:18][C:15]1[CH:14]=[CH:13][C: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:17][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 222697484-[3-(3,4-Dichloro-phenyl)propyl]phenylamineHCID 23404649Methyl 2-fluoro-4-methoxy-5-nitrobenzoate

Product 1

HCID 544753542-{4-[3-(3,4-Dichlorophenyl)propyl]phenylamino}-4-methoxy-5-nitrobenzoic acid methyl esterYield 42%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[3-(3,4-dichloro-phenyl)propyl]phenylamine (0.94 g, 3.3 mmol), 2-fluoro-4-methoxy-5-nitro-benzoic acid methyl ester (0.75 g, 3.3 mmol), and Et3N (0.46 mL) in CH3CN (30 mL) was heated to reflux for 120 hours. The reaction mixture was cooled to room temperature, diluted with CH2Cl2 and washed with saturated NaHCO3. The organic layer was dried (Na2SO4) and concentrated to give a solid. Recrystallization with MeOH yielded 0.67 g (1.37 mmol, 42%) of the desired product.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 120 hours
  3. washwashed with saturated NaHCO3
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a solid
  7. customRecrystallization with MeOH

Sources & evidence

ORD record
ord-e7c8b0ecbb034184bd65f760efa1b60e
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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