5-Cyclopropanecarbonyl-N-methyl-N-propyl-isophthalamic acid ethyl ester → 5-Cyclopropanecarbonyl-N-methyl-N-propyl-isophthalamic acid

HRID 732532Notes

Reaction equation

HRID 732532 reaction equation
C([O:3][C:4](=[O:23])[C:5]1[CH:17]=[C:16]([C:18]([CH:20]2[CH2:22][CH2:21]2)=[O: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+].C(O)C.O>[CH:20]1([C:18]([C:16]2[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=[C:5]([CH:17]=2)[C:4]([OH:23])=[O:3])=[O:19])[CH2:22][CH2:21]1

Participants

5

Reactant 1

HCID 688158375-Cyclopropanecarbonyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 688151165-Cyclopropanecarbonyl-N-methyl-N-propyl-isophthalamic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Stir the crude 5-cyclopropanecarbonyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (0.38 mmol) in 1 N NaOH (1 mL) and ethanol (1 mL) for 3 h at room temperature. Dilute the mixture with water (5 mL) and wash the aqueous solution with diethyl ether (2×3 mL). Acidify with 1 N HCl (1 mL) and extract with ethyl acetate (3×5 mL). Wash the combined organic layer with saturated aqueous sodium chloride, dry (sodium sulfate) and concentrate to give the title compound as a crude residue which is used in the next step without further purification.

Workup

  1. washwash the aqueous solution with diethyl ether (2×3 mL)
  2. extractionAcidify with 1 N HCl (1 mL) and extract with ethyl acetate (3×5 mL)
  3. washWash the combined organic layer with saturated aqueous sodium chloride
  4. dry with materialdry (sodium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-6f36dda4569d48ea9e53e32a84a2ea7c
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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