Sodium Hydroxide → 2-{4-[2-(3,4-Dimethyl-phenyl)-ethyl]phenylamino}-5-nitrobenzoic acid

HRID 488516Notes

Reaction equation

HRID 488516 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([CH3:29])[CH:23]=2)=[CH:16][CH:15]=1.[OH-].[Na+]>CCO.C1COCC1>[CH3:29][C:24]1[CH:23]=[C:22]([CH2:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:5]3[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=3[C:3]([OH:30])=[O:2])=[CH:15][CH:16]=2)[CH:27]=[CH:26][C:25]=1[CH3:28]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 541399142-{4-[2-(3,4-Dimethyl-phenyl)-ethyl]phenylamino)-5-nitrobenzoic acid methyl ester

Product 1

HCID 222697402-{4-[2-(3,4-Dimethyl-phenyl)-ethyl]phenylamino}-5-nitrobenzoic acidYield 95.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared 2-{4-[2-(3,4 dimethyl-phenyl)-ethyl]phenylamino}-5-nitrobenzoic acid methyl ester (1.12 g, 2.76 mmol), 1N NaOH (50 mL) in EtOH (50 mL) and THF (50 mL) using the procedure described in Example 2. This procedure yielded a yellow solid, 1.03 g (2.63 mmol, 81%) of the desired product. mp 214-216° C.

Sources & evidence

ORD record
ord-594448ce6c2749baa303d9c68d322fa9
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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