Sulfuric Acid → 2-Hydroxy-6-methyl-3-nitropyridine

HRID 66363Notes

Reaction equation

HRID 66363 reaction equation
N[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1.S(=O)(=O)(O)[OH:13].N([O-])=O.[Na+]>O>[CH3:11][C:4]1[NH:3][C:2](=[O:13])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 2260282-Amino-6-methyl-3-nitropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 5430292-Hydroxy-6-methyl-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 24 g. of 2-amino-6-methyl-3-nitropyridine in 25 ml. of concentrated sulfuric acid and 380 ml. of water was cooled to 0° C. and treated with 11 g. of sodium nitrite in 25 ml. of water. The temperature spontaneously rose to 45° C. After cooling, the precipitate of 6-methyl-3-nitro-2-pyridone was collected (m.p. 222°-223° C.) and used directly in the next step.

Workup

  1. additiontreated with 11 g
  2. customspontaneously rose to 45° C
  3. temperatureAfter cooling
  4. customthe precipitate of 6-methyl-3-nitro-2-pyridone was collected (m.p. 222°-223° C.)

Sources & evidence

ORD record
ord-3ae5f561ecfb4a0585066f857d993c18
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Reaction notes

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