Sodium Hydroxide → HCID 68817472, compound

HRID 732519Notes

Reaction equation

HRID 732519 reaction equation
C([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH2:18][OH: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+]>C1COCC1>[OH: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 14798Sodium HydroxideHCID 688164795-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 68817472HCID 68817472, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mix 5-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (1.0 g, 3.6 mmol), 1 N NaOH (25 mL) in THF (5 mL). Stir at room temperature overnight. Wash with diethyl ether (2×20 mL). Acidify the aqueous layer with 5 N HCl to about pH=2. Extract with ethyl acetate (2×20 mL), concentrate and purify (silica gel chromatography eluting with 1% acetic acid in ethyl acetate and hexanes) to give the title compound (0.80 g, 89%).

Workup

  1. washWash with diethyl ether (2×20 mL)
  2. extractionExtract with ethyl acetate (2×20 mL)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography eluting with 1% acetic acid in ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-c8f55fd5ab024a0ca517cacfad0b73a5
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…