Hydrochloric Acid → 3-(5-Dimethylcarbamoyl-pent-1-ynyl)-benzoic acid

HRID 643045Notes

Reaction equation

HRID 643045 reaction equation
C([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[C:12][CH2:13][CH2:14][CH2:15][C:16](=[O:20])[N:17]([CH3:19])[CH3:18])[CH:6]=1)C.[OH-].[Na+].Cl>>[CH3:19][N:17]([CH3:18])[C:16]([CH2:15][CH2:14][CH2:13][C:12]#[C:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([OH:21])=[O:3])=[O:20]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 112547173-(5-Dimethylcarbamoyl-pent-ynyl)benzoic acid ethyl ester

Product 1

HCID 114823353-(5-Dimethylcarbamoyl-pent-1-ynyl)-benzoic acidYield 74%

Procedure

3-(5-Dimethylcarbamoyl-pent-ynyl)benzoic acid ethyl ester (0.800 g, 2.78 mmol) was treated with sodium hydroxide 1M solution (6 mL) overnight. To the reaction mixture 7 mL of HCl 1M solution was added and the solvent was removed under vacuum. The residue was triturated with ethyl acetate, to give 3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid (24)(0.590 g, 2.05 mmol; yield 74%) as white off powder.

Workup

  1. customthe solvent was removed under vacuum
  2. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-8bfa9c88be3247228dc5cf516bb738e1
Source dataset
uspto-grants-2010_04
Patent number
US07696382B2

Reaction notes

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