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

HRID 488500Notes

Reaction equation

HRID 488500 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([O:13][CH3:14])=[CH:6][C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)=[CH:18][CH:17]=1>C1COCC1.[OH-].[Na+]>[Cl:32][C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][CH2:22][C:19]2[CH:20]=[CH:21][C:16]([NH:15][C:5]3[CH:6]=[C:7]([O:13][CH3:14])[C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=3[C:3]([OH:33])=[O:2])=[CH:17][CH:18]=2)[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

4

Reactant 1

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

Product 1

HCID 222697912-{4-[3-(3,4-Dichlorophenyl)propyl]phenylamino}-4-methoxy-5-nitrobenzoic acidYield 70.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-{4-[3-(3,4-dichlorophenyl)propyl]phenylamino}-4-methoxy-5-nitrobenzoic acid methyl ester (0.30 g, 0.061 mol) in THF (5 mL), 1N NaOH (aq.) (2.5 mL) was added, and the mixture was stirred for 36 hours at room temperature. The solvent was removed, and the residue was acidified with concentrated HCl to pH 3. The precipitate was collected by filtration and dried in vacuum for 16 hours. Recrystallization with MeOH gave the title compound as an orange solid 0.21 g (0.043 mol. 70%). mp 200-201° C.

Workup

  1. customThe solvent was removed
  2. filtrationThe precipitate was collected by filtration
  3. customdried in vacuum for 16 hours
  4. customRecrystallization with MeOH

Sources & evidence

ORD record
ord-3f0b46fdf0764748b85393b2d440e12c
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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