Sodium Hydroxide → N-[4-(3-Dimethylaminopyrrolidin-1-yl)phenyl]terephthalamic acid

HRID 1354783Notes

Reaction equation

HRID 1354783 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:26]=[CH:25][C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH:19]([N:22]([CH3:24])[CH3:23])[CH2:18]3)=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[CH3:23][N:22]([CH3:24])[CH:19]1[CH2:20][CH2:21][N:17]([C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:8](=[O:9])[C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:27])=[O:2])=[CH:26][CH:25]=3)=[CH:16][CH:15]=2)[CH2:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67148143N-[4-(3-Dimethylaminopyrrolidin-1-yl)phenyl]terephthalamic Acid Methyl Ester

Product 1

HCID 21105615N-[4-(3-Dimethylaminopyrrolidin-1-yl)phenyl]terephthalamic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[4-(3-Dimethylaminopyrrolidin-1-yl)phenyl]terephthalamic acid methyl ester (1.7 g) dissolved in methanol (20 ml) was stirred with sodium hydroxide solution (2N, 15 ml) at room temperature for 24 hours. If conversion is incomplete, it is also possible to heat to reflux. The organic solvent was distilled off, and the mixture was acidified with hydrochloric acid. The precipitate which separated out was filtered off with suction and dried. This resulted in the product with the molecular weight of 353.42 (C20H23N3O3); MS (ESI): 354 (M+H+).

Workup

  1. temperatureto heat to reflux
  2. distillationThe organic solvent was distilled off
  3. customThe precipitate which separated out
  4. filtrationwas filtered off with suction
  5. customdried
  6. customThis resulted in the product with the molecular weight of 353.42 (C20H23N3O3)

Sources & evidence

ORD record
ord-393ef0dbdb104d479f85de84571cf0cf
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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