Sulfuric Acid → 2-Hydroxy-6-methyl-5-nitropyridine

HRID 277985Notes

Reaction equation

HRID 277985 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[N:3]=1.S(=O)(=O)(O)[OH:13].[N+]([O-])([O-])=O.[Na+]>O>[O:13]=[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[NH:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24268Sodium NitrateHCID 2479766-Methyl-5-nitropyridin-2-amine

Product 1

HCID 5430532-Hydroxy-6-methyl-5-nitropyridineYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-amino-5-nitro-6-methylpyridine (40.24 g, 260 mmol) was added concentrated sulfuric acid (48 mL). The homogeneous solution was cooled to 0° C., and sodium nitrate (26.97 g, 390 mmol) dissolved in 120 mL of water was added. The reaction mixture was warmed to room temperature over 4 hours, then cooled to 0° C. The resulting ivory precipitate was collected, washed with cold water, and dried at 40° C. in vacuo overnight to provide 39.05 g (97%) of the title compound. EA calculated for C6H6N2O3: C, 46.76; H, 3.92; N, 18.18. Found: C, 46.49; H, 3.94; N, 17.99.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was warmed to room temperature over 4 hours
  3. temperaturecooled to 0° C
  4. customThe resulting ivory precipitate was collected
  5. washwashed with cold water
  6. customdried at 40° C. in vacuo overnight

Sources & evidence

ORD record
ord-ce861ade785846d4b549f7d2f2c21d94
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

Loading…