Hydrochloric Acid → 5-(Methyl-propylcarbamoyl)-isophthalic acid monoethyl ester

HRID 1436618Notes

Reaction equation

HRID 1436618 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:15]=[C:14]([C:16](=[O:22])[N:17]([CH3:21])[CH2:18][CH2:19][CH3:20])[CH:13]=[C:7]([C:8]([O:10]CC)=[O:9])[CH:6]=1)[CH3:2].[OH-].[Na+].Cl>C(O)C>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:15]=[C:14]([C:16](=[O:22])[N:17]([CH3:21])[CH2:18][CH2:19][CH3:20])[CH:13]=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688147335-(Methyl-propylcarbamoyl)-isophthalic acid diethyl ester

Product 1

HCID 688146805-(Methyl-propylcarbamoyl)-isophthalic acid monoethyl esterYield 75.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stir a solution of 5-(methyl-propylcarbamoyl)-isophthalic acid diethyl ester (2.02 g, 6.3 mmol), NaOH (0.25 g, 6.3 mmol) and ethanol (32 mL) at room temperature overnight. Add 0.2 N HCl (60 mL) and extract with ethyl acetate (2×50 mL). Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes with 1% acetic acid then 100% ethyl acetate with 1% acetic acid) to give the title compound as an oil (1.4 g, 75%).

Workup

  1. extractionextract with ethyl acetate (2×50 mL)
  2. dry with materialDry (magnesium sulfate)
  3. concentrationconcentrate
  4. custompurify (silica gel chromatography
  5. washeluting with 50:50 ethyl acetate

Sources & evidence

ORD record
ord-9847d721c17545bf873d71a3fb0553e2
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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