Potassium Carbonate → HCID 67218006, compound

HRID 450570Notes

Reaction equation

HRID 450570 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:24][O:25][CH2:26][CH2:27][CH2:28][OH:29]>CN(C=O)C.CCOC(C)=O>[CH3:24][O:25][CH2:26][CH2:27][CH2:28][O:29][C:2]1[N:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 741163-Methoxy-1-propanolHCID 61286363HCID 61286363, compound

Product 1

HCID 67218006HCID 67218006, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-chloro-3-nitro-2-(tetrahydro-2H-pyran-4-yloxy)pyridine (0.259 g, 1.00 mmol), K2CO3 (0.276 g, 2.00 mmol) and 3-methoxy-1-propanol (0.191 mL, 2.00 mmol) in DMF (3.0 mL) was heated at 60° C. for 6 hours and then at 100° C. for 24 hours. The reaction mixture was diluted with EtOAc, washed with water and brine (×2). The organic phase was dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by flash column chromatography (100% iso-hexane 75% iso-hexane/EtOAc) to afford an oil (0.17 g, 54%).

Workup

  1. washwashed with water and brine (×2)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash column chromatography (100% iso-hexane 75% iso-hexane/EtOAc)

Sources & evidence

ORD record
ord-afedc4fcb5f74b61b8cbd4caf9ab2680
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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