Nitric Acid → HCID 178432797, compound

HRID 1522591Notes

Reaction equation

HRID 1522591 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[CH3:10][C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][N:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:10][C:11]1[C:16]([N+:1]([O-:4])=[O:2])=[C:15]([OH:17])[CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 178429067HCID 178429067, compound

Product 1

HCID 178432797HCID 178432797, compound

Procedure

To a solution of fuming nitric acid (14.51 mL, 345 mmol), and sulfuric acid (14.45 ml, 271 mmol) was added 2-methylpyridin-4-ol (6.5 g, 59.6 mmol) portion wise at 25° C. and then stirred in oil bat set at 130° C. for 2 hours. The reaction was cooled to room temperature, poured over ice and the pH was adjusted to ˜7 using sodium carbonate. The mixture was cooled and a yellow precipitate formed which was then filtered and dried under vacuum for 2 hours in a rotovap set at 60° C. The solids were then slurried in methanol (100 mL) and sonicated 2×. The suspension was filtered and the solids discarded and the filtrate was concentrated under vacuum to give 2-methyl-3-nitropyridin-4-ol. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.28 (3H, br. s.) 6.18-6.42 (1H, m) 7.71 (1H, d, J=7.58 Hz) 12.09 (1H, br. s.); MS [M+H] found 155.0.

Workup

  1. additionpoured over ice
  2. temperatureThe mixture was cooled
  3. customa yellow precipitate formed which
  4. filtrationwas then filtered
  5. customdried under vacuum for 2 hours in a rotovap
  6. customset at 60° C
  7. customsonicated 2×
  8. filtrationThe suspension was filtered
  9. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-e4524bfe3f3049fca4187db44feab8d4
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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