Sulfuric Acid → 2-Hydroxy-4-methyl-3-nitropyridine

HRID 59957

Reaction equation

HRID 59957 reaction equation
N[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)[OH:13].N([O-])=O.[Na+]>O>[CH3:11][C:6]1[CH:5]=[CH:4][NH:3][C:2](=[O:13])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 2431662-Amino-4-methyl-3-nitropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 3453702-Hydroxy-4-methyl-3-nitropyridineYield 91.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Amino-4-methyl-3-nitropyridine (120 g, 0.78 mol) was suspended in water (1.6 L), a concentrated sulfuric acid (120 mL) was added dropwise, and the clear yellow solution was cooled to 0° C. in an ice bath. Sodium nitrite (98 g, 1.42 mol) dissolved in water (250 mL) was added slowly bellow the liquid surface of the reaction solution through a long stem funnel. The reaction mixture was stirred at room temperature for 2 h and was boiled up until no further emission of a brown gas was observed. The reaction solution was cooled, filtered, and dried to obtain the title compound (yield 91.6%).

Workup

  1. additionwas added slowly bellow the liquid surface of the reaction solution through a long stem funnel
  2. temperatureThe reaction solution was cooled
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-f15fc11e2880465b9400f455925e6634
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Linked notes

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