Methanol → 2-Amino-6-methoxy-3-nitropyridine

HRID 854068Notes

Reaction equation

HRID 854068 reaction equation
[CH3:1][O-:2].[Na+].CO.[NH2:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9](Cl)[N:8]=1>O>[NH2:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:9]([O:2][CH3:1])[N:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 10942334Sodium Methoxide

Product 1

HCID 38524282-Amino-6-methoxy-3-nitropyridineYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

Sodium methoxide, 7.78 gm (0.144 mole) and methanol 50.0 ml were mixed and cooled to 15° C. To this solution, 25.0 gm of 2-amino-6-chloro-3-nitropyridine (0.144 mole) was added while maintaining the temperature at 15° C. by external cooling. The resulting mixture was heated to 25°–30° C. and maintained at this temperature for 4–5 hrs with constant stirring. The completion of reaction was monitored by TLC. After the completion of reaction, the reaction mixture was poured in water. The precipitate thus obtained was filtered and washed with water. On drying 21.0 gm of 2-amino-3-nitro-6-methoxypyridine (86.5% yield) was obtained, with the HPLC purity of 99.0%. Melting point 167°–169° C.; 1HNMR (CDCl3) δ3.89 ppm (s, -3H, OCH3), 66.14–6.16 ppm (d, 1H), 68.24–8.27 ppm (d, 1H), 68.16 ppm (s, -2H, —NH2)

Workup

  1. temperaturewhile maintaining the temperature at 15° C. by external cooling
  2. temperatureThe resulting mixture was heated to 25°–30° C.
  3. temperaturemaintained at this temperature for 4–5 hrs with constant stirring
  4. customThe completion of reaction
  5. customAfter the completion of reaction
  6. customThe precipitate thus obtained
  7. filtrationwas filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-e85ef355fb0f477f88ab9f637bf2cb26
Source dataset
uspto-grants-2007_08
Patent number
US07256295B2

Reaction notes

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