Sodium Hydroxide → HCID 68462653, compound

HRID 2250398Notes

Reaction equation

HRID 2250398 reaction equation
C[C:2]1[C:3]([O:15][CH3:16])=[C:4]([CH3:14])[C:5]([C:11]([OH:13])=[O:12])=[N:6][C:7]=1[C:8]([OH:10])=[O:9].[OH-].[Na+]>O.CO>[CH3:14][C:4]1[C:5]([C:11]([OH:13])=[O:12])=[N:6][C:7]([C:8]([OH:10])=[O:9])=[CH:2][C:3]=1[O:15][CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 68465340HCID 68465340, compound2×

Product 1

HCID 68462653HCID 68462653, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3.0 g of dimethyl 4-methoxy-pyridin-2,6-dicarboxylic acid (compound F6) are dissolved in 280 ml of water and 420 ml of methanol. After cooling to 0° C., 14.65 ml of a sodium hydroxide solution (strength 1.0 M) is added dropwise (15 min). After 1 h, the mixture is allowed to warm up to room temperature and is stirred for further 21 h during which time 2.0 ml of sodium hydroxide solution are gradually added. Subsequently, 6.5 g of acidic ion exchange resin (Amberlite IR-120 [H+]) are added for neutralization. Thereafter, the mixture is filtered and the filtrate is concentrated in vacuum to yield 2.8 g of the title compound as a colorless oil. TSP-MS: 212.1 [MH+]. TLC: Rf=0.1-0.2 (dichlormethane/methanol 5:1, 3.0 vol.-% acetic acid).

Workup

  1. temperatureto warm up to room temperature
  2. additionare gradually added
  3. filtrationThereafter, the mixture is filtered
  4. concentrationthe filtrate is concentrated in vacuum

Sources & evidence

ORD record
ord-43947b320dbd4e21902929a9455ce1f0
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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