2-Chloro-5-nitropyridine → 2-Isopropoxy-5-nitropyridine

HRID 419016Notes

Reaction equation

HRID 419016 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH:11]([O:14][Na])([CH3:13])[CH3:12]>CC(O)C>[O:14]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[CH:11]([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 178459997HCID 178459997, compound

Product 1

HCID 120361742-Isopropoxy-5-nitropyridineYield 79.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A freshly oven dried 500 mL round-bottom flask was charged with 2-chloro-5-nitropyridine (5.0 g, 31.6 mmol) and anhydrous iPrOH (50 mL). The resultant solution was cooled in an ice bath and iPrONa (50 mmol) in iPrOH (250 mL) added slowly, followed by stirring at the same temperature for 30 min and then at room temperature for 14 h. The reaction was quenched with H2O (5 mL), filtered through celite, and concentrated under reduced pressure. The residue was diluted with EtOAc and washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified through automated normal-phase chromatography to afford 2-isopropoxyl-5-nitropyridine (4.6 g, 79%) which was used directly for the next step: 1H NMR (400 MHz, CDCl3) δ 9.02 (d, 1H), 8.30 (dt, 1H), 6.75 (d, 1H), 5.40 (sep, 1H), 1.38 (d, 6H); MS (ES) (M++H) expect 183.1, found 183.1.

Workup

  1. customA freshly oven dried 500 mL round-bottom flask
  2. waitat room temperature for 14 h
  3. customThe reaction was quenched with H2O (5 mL)
  4. filtrationfiltered through celite
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was diluted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified

Sources & evidence

ORD record
ord-461a6c747748489fa343df0553d0b2da
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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