Nitric Acid → HCID 178526712, compound

HRID 535207Notes

Reaction equation

HRID 535207 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[N+:9]([O-])([OH:11])=[O:10]>C(O)(=O)C>[NH2:9][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[N+:3]([O-:8])[CH:4]=1.[N+:9]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[N+:3]([O-:8])[CH:4]=1)([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 178526252HCID 178526252, compound

Product 2

HCID 178507784HCID 178507784, compoundHCID 178526712HCID 178526712, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

5-amino-2-hydroxypyridine-N-oxide was prepared as follows. One hundred grams of the 2-hydroxypyridine-N-oxide were dissolved in 500 mL of acetic acid with warming. The solution was cooled to approximately 10° C., and 65 mL of 70% nitric acid was added slowly to keep the temperature below 35° C. The mixture was stirred for an additional 30 min and the product was collected by filtration. After washing with acetic acid, and then water, the product was dried under vacuum at 70° C., to give 5-nitro-2-hydroxypyridine-N-oxide (95.9 g, 68% yield). 1HNMR data for this compound (DMSO) was as follows: δ 9.2 (d, 1H), 8.1 (dd, 1H), 6.6 (d, 1H).

Workup

  1. temperaturewith warming
  2. customthe temperature below 35° C
  3. filtrationthe product was collected by filtration
  4. washAfter washing with acetic acid
  5. dry with materialwater, the product was dried under vacuum at 70° C.

Sources & evidence

ORD record
ord-e4a82bc9995b4adb869d1b6499dd8fd1
Source dataset
uspto-grants-2014_10
Patent number
US08858695B2

Reaction notes

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