Ammonia → HCID 178526833, compound

HRID 1986344Notes

Reaction equation

HRID 1986344 reaction equation
N.CC(C)([O-:5])C.[K+].[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16].C(OO)(C)(C)C>C1COCC1>[Cl:8][C:9]1[C:10]([N+:15]([O-:17])=[O:16])=[CH:11][N:12]=[C:13]([OH:5])[CH:14]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6410tert-Butyl hydroperoxideHCID 27357814-Chloro-3-nitropyridineHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 178526833HCID 178526833, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-35 °C

Procedure

THF (500 mL) was cooled to −78° C. and anhydrous NH3 (˜200 mL) was condensed into the THF. Potassium t-butoxide (71.0 g, 630 mmol) was added and the mixture was allowed to warm to ˜−35° C. The product from Step 1 (40.0 g, 250 mmol) was cooled to 0° C. in THF (200 mL) and a solution of t-BuOOH (5 M in decane, 50 mL, 250 mmol) was added over 5 min. This solution was then added dropwise to the KOt-Bu solution prepared above over 1 h, then stirred for 2 h at −35° C. and then carefully quenched with ˜50 mL of sat. NH4Cl solution. The mixture was allowed to vent and warm to rt overnight, then the organics were concentrated and the residue made acidic with NH4Cl solution and filtered. The solid was washed with cold H2O and dried to give the title compound as a dark brown solid (35 g, 80%).

Workup

  1. customprepared above over 1 h
  2. customcarefully quenched with ˜50 mL of sat. NH4Cl solution
  3. temperaturewarm to rt overnight
  4. concentrationthe organics were concentrated
  5. filtrationfiltered
  6. washThe solid was washed with cold H2O
  7. customdried

Sources & evidence

ORD record
ord-42745965698244f59b83b61341809bc7
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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