Hydrochloric Acid → N-Methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-N-propyl-isophthalamic acid

HRID 1436638Notes

Reaction equation

HRID 1436638 reaction equation
C([O:3][C:4](=[O:24])[C:5]1[CH:17]=[C:16]([C:18]2[O:22][N:21]=[C:20]([CH3:23])[N:19]=2)[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)C.[OH-].[Li+].Cl>C1COCC1>[CH3:14][N:10]([CH2:11][CH2:12][CH3:13])[C:8](=[O:9])[C:7]1[CH:6]=[C:5]([CH:17]=[C:16]([C:18]2[O:22][N:21]=[C:20]([CH3:23])[N:19]=2)[CH:15]=1)[C:4]([OH:24])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68815853N-Methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 68815074N-Methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-N-propyl-isophthalamic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stir a solution of N-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-N-propyl-isophthalamic acid ethyl ester (135 mg, 0.4 mmol), 1 N lithium hydroxide (1.6 mL, 1.6 mmol) and THF (1.6 mL) at room temperature overnight. Add 1 N HCl (20 mL) and extract with ethyl acetate (3×20 mL). Dry (magnesium sulfate) and concentrate to give the title compound.

Workup

  1. extractionextract with ethyl acetate (3×20 mL)
  2. dry with materialDry (magnesium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-4c47154cb47841e5a31cbbce5309d06d
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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