Methanol → 5-Bromo-2-methoxy-3-nitropyridine

HRID 445613Notes

Reaction equation

HRID 445613 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[CH3:12][OH:13]>>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([O:13][CH3:12])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 887Methanol2×HCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 156456645-Bromo-2-methoxy-3-nitropyridine

Conditions

Temperature
0 °C

Procedure

In a vial are introduced 1 ml of MeOH and 50.8 mg (2.21 mmol) of Na. After dissolution of the metal, the solution was added to a suspension of 5-bromo-2-chloro-3-nitropyridine (Matrix, Columbia, USA, 500 mg, 2.11 mmol) in MeOH (2 ml). The reaction mixture is stirred for 1 h at 0° C. and for 15 h at rt, then concentrated and quenched with water. The precipitate was filtered, washed with water (2×) and dried under vacuum to give the title compound as a pale yellow solid (HPLC: tR 3.06 min (Method A).

Workup

  1. dissolutionAfter dissolution of the metal
  2. concentrationconcentrated
  3. customquenched with water
  4. filtrationThe precipitate was filtered
  5. washwashed with water (2×)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-1113385c49654c25adaa1c1eb841d0e4
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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