Methanol → 3-Bromo-2-methoxy-4-methyl-5-nitropyridine

HRID 1909067Notes

Reaction equation

HRID 1909067 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[CH3:8].[CH3:13][OH:14].C[O-].[Na+]>O>[Br:1][C:2]1[C:3]([O:14][CH3:13])=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 401519173-Bromo-2-chloro-4-methyl-5-nitropyridine

Product 1

HCID 665992573-Bromo-2-methoxy-4-methyl-5-nitropyridineYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-Bromo-2-chloro-4-methyl-5-nitro-pyridine (5.00 g, 19.9 mmol) in anyhdrous Methanol was added a 25% methanolic NaOMe solution (10.7 mL, 2.5 eq). The reaction was stirred at room temperature for 24 hr. The solvent was removed under reduced pressure giving a solid. Water (100 mL) was added to the flask and the flask sonicated for 5 minutes. The precipitate was filtered and washed with water (50 mL) giving a beige powder. The aqueous mother liquor was extracted with EtOAc (1×), the organic washed with brine, and dried. The two solids were combined giving 3-Bromo-2-methoxy-4-methyl-5-nitro-pyridine (2.75 g, 10.6 mmol, 53%). 1H NMR (400 MHz, CDCl3) δ 8.75 (s, 1H), 4.12 (s, 3H), 2.72 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customgiving a solid
  3. customthe flask sonicated for 5 minutes
  4. filtrationThe precipitate was filtered
  5. washwashed with water (50 mL)
  6. customgiving a beige powder
  7. extractionThe aqueous mother liquor was extracted with EtOAc (1×)
  8. washthe organic washed with brine
  9. customdried

Sources & evidence

ORD record
ord-b49fd49c47d34c139b6a1b35dafa96a1
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

Loading…