Ammonia → 2-Isopropyl-5-nitropyridine

HRID 470116Notes

Reaction equation

HRID 470116 reaction equation
C[N:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]1=O.[CH3:15][CH:16](C)[C:17](=O)C.N>CO>[CH:16]([C:7]1[CH:6]=[CH:5][C:4]([N+:11]([O-:13])=[O:12])=[CH:3][N:2]=1)([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 112513-Methyl-2-butanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 450963212-Isopropyl-5-nitropyridineYield 28.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 1-methyl-3,5-dinitro-2-pyridone (8.0 g, 40 mmol) in methyl alcohol (20 mL) was added dropwise 3-methyl-2-butanone (5.1 mL, 48 mmol), followed by ammonia solution in methyl alcohol (10.0 g, 17%, 100 mmol). The reaction mixture was heated at 70° C. for 2.5 h under atmospheric pressure. The solvent was removed under vacuum and the residual oil was dissolved in CH2Cl2, and then filtered. The filtrate was dried over Na2SO4 and concentrated to afford 2-isopropyl-5-nitro-pyridine (1.88 g, 28%).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residual oil was dissolved in CH2Cl2
  3. filtrationfiltered
  4. dry with materialThe filtrate was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-47d1cfcfb6b1412392cd0ff331ae130d
Source dataset
uspto-grants-2014_01
Patent number
US08629162B2

Reaction notes

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