Lithium Hydroxide → N-Methyl-N-propyl-5-vinyl-isophthalamic acid

HRID 1436634Notes

Reaction equation

HRID 1436634 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:16]=[C:15]([CH:17]=[CH2:18])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[OH-].[Li+]>C1COCC1>[CH3:13][N:9]([CH2:10][CH2:11][CH3:12])[C:7](=[O:8])[C:6]1[CH:5]=[C:4]([CH:16]=[C:15]([CH:17]=[CH2:18])[CH:14]=1)[C:3]([OH:19])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68814555N-Methyl-N-propyl-5-vinyl-isophthalamic acid methyl ester

Product 1

HCID 68815025N-Methyl-N-propyl-5-vinyl-isophthalamic acidYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stir a solution of N-methyl-N-propyl-5-vinyl-isophthalamic acid methyl ester (78 mg, 0.3 mmol), 1 N lithium hydroxide (1.5 mL, 1.5 mmol), and THF (1.5 mL) at room temperature overnight. Add water and extract with ethyl acetate. Acidify the aqueous with 5 N HCl, extract with ethyl acetate, dry (magnesium sulfate) and concentrate to give the title compound (52 mg, 70%).

Workup

  1. extractionAdd water and extract with ethyl acetate
  2. extractionextract with ethyl acetate
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-e841ff79921a4854ba8a9e08e907c90f
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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