Potassium Carbonate → N-[2,2-bis(methyloxy)ethyl]-6-(methyloxy)-3-nitro-2-pyridinamine

HRID 657100Notes

Reaction equation

HRID 657100 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH2:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C=O)C>[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH:17][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 89728Aminoacetaldehyde dimethyl acetalHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 68812011N-[2,2-bis(methyloxy)ethyl]-6-(methyloxy)-3-nitro-2-pyridinamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-chloro-6-(methyloxy)-3-nitropyridine (10 g, 53 mmol), aminoacetaldehyde dimethylacetal (5.6 g, 6.2 ml, 53 mmol) and potassium carbonate (7.4 g, 53 mmol) in acetonitrile (100 mL) and DMF (10 mL) was heated at 40° C. for 30 minutes. The mixture was filtered and extracted with DCM and brine. The organic extract was added to a silica column which was then eluted with 0-100% ethyl acetate in hexane affording a yellow solid (12.4 g, 90%).

Workup

  1. filtrationThe mixture was filtered
  2. extractionextracted with DCM and brine
  3. extractionThe organic extract
  4. additionwas added to a silica column which
  5. washwas then eluted with 0-100% ethyl acetate in hexane affording a yellow solid (12.4 g, 90%)

Sources & evidence

ORD record
ord-1c9e67252a8b40a29ea688340c8bcde4
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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