N,N-Dimethylglycine → HCID 178526841, compound

HRID 1620096Notes

Reaction equation

HRID 1620096 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O.[OH:19][C:20]1[C:25](I)=[CH:24][C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1>[Cu](I)I.C(OCC)(=O)C.O.CN(C)C(=O)C>[OH:19][C:20]1[C:25]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:24][C:23]([N+:27]([O-:29])=[O:28])=[CH:22][N:21]=1

Participants

9

Reactant 4

HCID 673N,N-DimethylglycineHCID 1048PyrazoleHCID 10796Cesium carbonateHCID 178526840HCID 178526840, compound

Product 1

HCID 178526841HCID 178526841, compoundYield 22.6%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

Pyrazole (0.60 g), cesium carbonate (3.6 g), N,N-dimethylglycine (0.76 g), and copper iodide (I) (0.76 g) were added to an N,N-dimethylacetamide (20 ml) solution containing 2-hydroxy-3-iodo-5-nitropyridine (2.00 g) in a nitrogen atmosphere, followed by stirring at 90° C. for 2.5 hours. The reaction solution was adjusted to room temperature, water and ethyl acetate were added, and an insoluble precipitate was removed. The pH was adjusted to pH 2 with the addition of 6M hydrochloric acid. Then, organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure. Ethyl acetate was added to the obtained residue, a solid precipitate was collected by filtration, and a green solid of 2-hydroxy-5-nitro-3-(1H-pyrazol-1-yl)pyridine (0.35 g) was thus obtained. Thereafter, the filtrate was collected, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1 to 0:1), and a light green solid of 2-hydroxy-5-nitro-3-(1H-pyrazol-1-yl)pyridine (1.02 g) was thus obtained.

Workup

  1. customwas adjusted to room temperature
  2. customan insoluble precipitate was removed
  3. additionThe pH was adjusted to pH 2 with the addition of 6M hydrochloric acid
  4. washThen, organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. additionEthyl acetate was added to the obtained residue
  8. filtrationa solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-cebef4282543477c91dbcbcfb0bf9640
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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