Nitric Acid → HCID 178428771, compound

HRID 1887999Notes

Reaction equation

HRID 1887999 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([OH:9])=[N:6][C:7]=1[CH3:8].S(=O)(=O)(O)O.[N+:15]([O-])([OH:17])=[O:16]>>[CH3:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[C:5]([OH:9])=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 178426912HCID 178426912, compound

Product 1

HCID 178428771HCID 178428771, compoundYield 54%

Procedure

A mixture of 5,6-dimethylpyridin-2-ol (9.57 g, 0.078 mol) and concentrated sulfuric acid (116 mL) cooled in an ice bath was treated with 70% nitric acid (6.5 mL) in a dropwise manner so that the reaction temperature remains below 15° C., after which the reaction was stirred for a further 1 hour. The mixture was poured into ice-water (300 ml), stirred for 5 minutes then filtered, washed with water (60 mL) and dried under vacuum at 60° C. to yield 5,6-dimethyl-3-nitropyridin-2-ol (7.09 g, 54%). 400 M Hz 1H NMR (DMSO-d6) δ: 12.74 (s, 1H), 8.32 (s, 1H), 2.26 (s, 3H), 2.03 (s, 3H).

Workup

  1. temperaturecooled in an ice bath
  2. customremains below 15° C.
  3. stirringstirred for 5 minutes
  4. filtrationthen filtered
  5. washwashed with water (60 mL)
  6. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-0232375abe4c4220b773af1c0634d802
Source dataset
uspto-grants-2013_08
Patent number
US08501770B2

Reaction notes

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