Sodium Hydroxide → HCID 68814473, compound

HRID 1436682Notes

Reaction equation

HRID 1436682 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:16]=[C:15]([C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:18])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[OH-].[Na+]>CO.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]([C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[O:18])[CH:14]=1)[C:3]([OH:25])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68814474HCID 68814474, compound

Product 1

HCID 68814473HCID 68814473, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Chill a solution of N-methyl-N-propyl-5-(pyridine-3-carbonyl)-isophthalamic acid methyl ester (0.070 g, 0.206 mmol) in MeOH (1 mL) and THF (1 mL) in an ice bath. Add 1 N NaOH (0.62 mL, 0.62 mmol) and stir at room temperature for 2 h. Acidify the solution to about pH=2 and concentrate to one half of the solvent. Partition the residue between ethyl acetate and H2O. Extract the aqueous layer with ethyl acetate (2×15 mL). Wash the combined organic extract with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound (72%).

Workup

  1. concentrationconcentrate to one half of the solvent
  2. customPartition the residue between ethyl acetate and H2O
  3. extractionExtract the aqueous layer with ethyl acetate (2×15 mL)
  4. washWash the combined
  5. extractionorganic extract with saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-900507c11f874ed1b384c6ae268ee0a4
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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