Sodium Hydroxide → HCID 67132945, compound

HRID 1518178Notes

Reaction equation

HRID 1518178 reaction equation
[CH2:1]([C:8]1([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:16]([O-])([O-:18])=[O:17].[K+].[OH-].[Na+]>OS(O)(=O)=O>[N+:16]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][C:8]2([NH:11][C:12](=[O:15])[CH2:13][CH3:14])[CH2:9][CH2:10]2)=[CH:3][CH:4]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 67132938HCID 67132938, compound

Product 1

HCID 67132945HCID 67132945, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To H2SO4(20 ml) at 0-10° C. N-(1-benzyl-cyclopropyl)-propionamide (2 g, 9.84 mmol) was slowly added. The mixture was stirred until a clear solution was obtained. Then KNO3 (1 g, 9.89 mmol) was added in portions at 0-5° C. The mixture was stirred at room temperature for 16 h after which it was poured into ice water, and 50% NaOH was added. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and the solvent evaporated under reduced pressure. The residue was triturated with isopropylether and the precipitate filtered and dried in vacuo to give the product as a brown powder (900 mg, 37%).

Workup

  1. customat 0-10° C
  2. customwas obtained
  3. stirringThe mixture was stirred at room temperature for 16 h after which it
  4. additionwas added
  5. extractionThe aqueous layer was extracted three times with ethyl acetate
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated under reduced pressure
  10. customThe residue was triturated with isopropylether
  11. filtrationthe precipitate filtered
  12. customdried in vacuo

Sources & evidence

ORD record
ord-8fa7c3b2fe574c15985553ba65195081
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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