Water → HCID 15239998, compound

HRID 1653649Notes

Reaction equation

HRID 1653649 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=[O:12])[C:8]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CI.[C:24](=O)([O-])O.[Na+].O>CN(C=O)C>[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:24])=[O:12])[C:8]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 15239997HCID 15239997, compound

Product 1

HCID 15239998HCID 15239998, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g (5.2 mmol) of the obtained 6-acetylamino-3-benzyloxypicolinic acid and 1.0 g (7 mmol) of methyl iodide were dissolved in 100 ml of DMF, and 20 ml of an aqueous solution of 0.53 g (6.3 mmol) of sodium hydrogen carbonate was added thereto. The mixture was reacted at 60° C. for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The crystals thereby obtained was washed with diisopropyl ether to obtain methyl 6-acetylamino-3-benzyloxypicolinate.

Workup

  1. customThe mixture was reacted at 60° C. for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe crystals thereby obtained
  7. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-e5aa39c6d85a438f84a308c1a6a65665
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

Loading…