Potassium Carbonate → 2-Methoxy-3,6-dimethyl-5-nitropyridine

HRID 386501Notes

Reaction equation

HRID 386501 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9]C(OC(C)(C)C)=O)[C:6]([N+:17]([O-:19])=[O:18])=[CH:5][C:4]=1[CH3:20].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:20])=[CH:5][C:6]([N+:17]([O-:19])=[O:18])=[C:7]([CH3:9])[N:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 44596705Tert-butyl 2-(6-methoxy-5-methyl-3-nitropyridin-2-yl)acetate

Product 1

HCID 445964872-Methoxy-3,6-dimethyl-5-nitropyridineYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of tert-butyl 2-(6-methoxy-5-methyl-3-nitropyridin-2-yl)acetate (62.5 g, 276 mmol), K2CO3 (20.0 g, 145 mmol), and DMF (100 mL) was heated with stirring in a hot water bath to 90° C. for 1 h. Gas evolution was noted during the heating period and had ceased after 1 hour. The mixture was poured into stirred ice water (600 mL), with washing of the reaction flask with a small volume of acetone. The resulting precipitate was collected by filtration and air dried to give 2-methoxy-3,6-dimethyl-5-nitropyridine (48.5 g, 96% yield) as a tan solid: 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 4.02 (s, 3H), 2.76 (d, 3H), 2.19 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 163.37, 151.63, 139.44, 135.02, 119.39, 54.45, 24.18, 15.16. An analytical sample was recrystallized from hexanes to give tan needles: mp 85.9-90.5° C. Anal. calcd. for C8H10N2O3: C, 52.74; H, 5.53; N, 15.37. Found: C, 52.82; Fr, 5.28; N, 15.45.

Workup

  1. temperaturewas heated
  2. waithad ceased after 1 hour
  3. additionThe mixture was poured
  4. washwith washing of the reaction flask with a small volume of acetone
  5. filtrationThe resulting precipitate was collected by filtration and air
  6. customdried

Sources & evidence

ORD record
ord-aeb653f360ec4331a02e37dd4175966d
Source dataset
uspto-grants-2013_02
Patent number
US08372847B2

Reaction notes

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