Sodium Hydroxide → 2-{4-[5-(3,4-Dichlorophenyl)pentyl]phenylamino}4-methoxy-5-nitrobenzoic acid

HRID 488513Notes

Reaction equation

HRID 488513 reaction equation
C[O:2][C:3](=[O:35])[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][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)=[CH:18][CH:17]=1.[OH-].[Na+]>C1COCC1>[Cl:34][C:29]1[CH:28]=[C:27]([CH2:26][CH2:25][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:35])=[O:2])=[CH:17][CH:18]=2)[CH:32]=[CH:31][C:30]=1[Cl:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 540571152-{4-[5-(3,4-Dichlorophenyl)-pentyl]phenylamino}4-methoxy-5-nitrobenzoic acid methyl ester

Product 1

HCID 222698172-{4-[5-(3,4-Dichlorophenyl)pentyl]phenylamino}4-methoxy-5-nitrobenzoic acidYield 42.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from 2-{4-[5-(3,4-dichlorophenyl)-pentyl]phenylamino}-4-methoxy-5-nitrobenzoic acid methyl ester (145 mg, 0.28 mmol) and 1N NaOH (aq.) (0.56 mL) in THF (1.2 mL) using the procedure described in Example 2. Purification by flash chromatography (silica gel, 10% MeOH/CH2Cl2), then recrystallization with MeOH yielded 58 mg (0.12 mmol, 41%) of the desired product. mp 192-193° C.

Workup

  1. customPurification by flash chromatography (silica gel, 10% MeOH/CH2Cl2)
  2. customrecrystallization with MeOH

Sources & evidence

ORD record
ord-563f1884a2da435085ac25301f0f9100
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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