Lithium Hydroxide → 5-Fluoromethyl-N-methyl-N-propyl-isophthalamic acid

HRID 1436630Notes

Reaction equation

HRID 1436630 reaction equation
C([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH2:18][F:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)C.[OH-].[Li+]>C1COCC1>[F:19][CH2:18][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:20])=[O:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68814490HCID 68814490, compound

Product 1

HCID 688162355-Fluoromethyl-N-methyl-N-propyl-isophthalamic acidYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Stir a solution of 5-fluoromethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (73 mg, 0.26 mmol), 1 N lithium hydroxide (1.3 mL, 1.3 mmol) and THF (1.3 mL) at room temperature overnight. Add water (10 mL) and extract with dichloromethane (3×10 mL). Acidify the aqueous with 5 N HCl (260 μL), extract with dichloromethane (3×10 mL), dry (magnesium sulfate) and concentrate to give the title compound (56 mg, 85%).

Workup

  1. extractionAdd water (10 mL) and extract with dichloromethane (3×10 mL)
  2. extractionextract with dichloromethane (3×10 mL)
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-4a4222a91c614e16a9978e0fb96e8bcd
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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