Water → HCID 15240000, compound

HRID 1653655Notes

Reaction equation

HRID 1653655 reaction equation
[C:1]([N:4]([C:6]1[N:11]=[C:10]([C:12]([O:14]C)=[O:13])[C:9]([O:16][C:17]2[N:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[N:18]=2)=[CH:8][CH:7]=1)C)(=O)C.[OH-].[K+].O>CO>[CH3:24][O:23][C:21]1[CH:20]=[C:19]([O:25][CH3:26])[N:18]=[C:17]([O:16][C:9]2[C:10]([C:12]([OH:14])=[O:13])=[N:11][C:6]([NH:4][CH3:1])=[CH:7][CH:8]=2)[N:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium Hydroxide2×HCID 15240001HCID 15240001, compound

Product 1

HCID 15240000HCID 15240000, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

195.6 g (0.54 mol) of methyl 6-(N-acetyl-N-methylamino)-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate was dissolved in 1.5 l of methanol. The solution was added to 335 g of a 20% potassium hydroxide aqueous solution, and the mixture was stirred for one hour at 50° C. The reaction solution was concentrated, and 1 l of ice water was added thereto. The mixture was acidified (to about pH4) with an aqueous citric acid solution and left to cool. Precipitated crystals were collected by filtration and washed with cool water and diisopropyl ether. Then, the crystals were dissolved in 1 l of methanol, and 45.6 g (0.69 mol) of potassium hydroxide and 50 ml of water were added thereto. The mixture was stirred at room temperature for 28 hours. The reaction solution was concentrated, and ice water was added thereto. The mixture was acidified with an aqueous citric acid solution to obtain crude crystals. The crystals were washed with diisopropyl ether and then dried under reduced pressure at 90° C. for 24 hours to obtain 112 g (yield: 68%) of the desired product as a white powder.

Workup

  1. concentrationThe reaction solution was concentrated
  2. addition1 l of ice water was added
  3. waitleft
  4. temperatureto cool
  5. customPrecipitated crystals
  6. filtrationwere collected by filtration
  7. washwashed with cool water and diisopropyl ether
  8. dissolutionThen, the crystals were dissolved in 1 l of methanol
  9. stirringThe mixture was stirred at room temperature for 28 hours
  10. concentrationThe reaction solution was concentrated
  11. additionice water was added
  12. customto obtain crude crystals
  13. washThe crystals were washed with diisopropyl ether
  14. customdried under reduced pressure at 90° C. for 24 hours

Sources & evidence

ORD record
ord-f6d2d394ae17469c972290699af10fcc
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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