Hydrochloric Acid → 5-Acetyl-N-methyl-N-propyl-isophthalamic acid

HRID 732567Notes

Reaction equation

HRID 732567 reaction equation
C([O:3][C:4](=[O:21])[C:5]1[CH:17]=[C:16]([C:18](=[O:20])[CH3:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)C.[OH-].[Na+].Cl>C(O)C>[C:18]([C:16]1[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=[C:5]([CH:17]=1)[C:4]([OH:21])=[O:3])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688169505-Acetyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 575292855-Acetyl-N-methyl-N-propyl-isophthalamic acidYield 101.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treat a solution of 5-acetyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (196 mg, 0.67 mmol) in ethanol (7 mL) at room temperature with 2 N NaOH (0.5 mL, 1.0 mmol) for 12 h. Acidify to about pH=3 using 1 N HCl. Extract with ethyl acetate (50 mL), dry (magnesium sulfate) and concentrate to give the title compound (179 mg, 95%).

Workup

  1. extractionExtract with ethyl acetate (50 mL)
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-41bc906b1a6c4ca69e9b28db121bea72
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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