3-Hydroxy-2-nitropyridine → HCID 57742094, compound

HRID 1879998Notes

Reaction equation

HRID 1879998 reaction equation
[OH:1][C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:11][C:12]([CH3:19])([CH2:17]O)[C:13]([O:15][CH3:16])=[O:14].CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[CH3:11][C:12]([CH3:19])([CH2:17][O:1][C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 270573-Hydroxy-2-nitropyridineHCID 84152Methyl 3-hydroxypivalateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 57742094HCID 57742094, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Hydroxynitropyridine (10.0 g, 64 mmol), methyl 2,2-dimethyl-3-hydroxypropionate (9.29 g, 70.4.0 mmol) and PPH3 (15.15 g, 76.8 mmol) were dissolved in dioxane (500 mL). DIAD (14.5 mL, 76.8 mmol) was added at 0° C. over 5 min and the mixture was stirred at rt for 4 h then refluxed overnight. The mixture was evaporated, dissolved in ethyl acetate, washed with water, dried over magnesium sulfate and evaporated in vacuo to afford the title compound (9.1 g, 61%). 1H NMR (300 MHz, DMSO-d6) δ 8.22 (d, J=1.4 Hz, 1H), 7.98 (d, J=2.0 Hz, 1H), 7.70 (m, 1H), 4.43 (s, 2H), 3.59 (s, 3H), 1.17 (s, 6H)

Workup

  1. temperaturethen refluxed overnight
  2. customThe mixture was evaporated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-3e9b2c4060b34dd1b516786d10d5caea
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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