Hydrazinium chloride → HCID 178470413, compound

HRID 872929Notes

Reaction equation

HRID 872929 reaction equation
O/[C:2](=[C:8]1/[CH2:9][O:10][CH2:11][CH2:12][C:13]/1=O)/[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl.[NH2:16][NH2:17]>CO>[N:16]1[NH:17][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]2[CH2:9][O:10][CH2:11][CH2:12][C:13]=12

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 131732554HCID 131732554, compound

Product 1

HCID 178470413HCID 178470413, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-ethyl 2-hydroxy-2-(4-oxo-2H-pyran-3(4H, 5H, 6H)-ylidene)acetate (2.5 g, 12.49 mmol) was dissolved in methanol (10 ml). Hydrazine hydrochloride (2.57 g, 37.5 mmol) was added and the resulting mixture was refluxed for one hour. The mixture was allowed to warm to RT and the solvent was evaporated. The residue was dissolved in DCM and extracted twice with water. The organic layer was dried with Na2SO4, filtered and evaporated. The product was purified with flash chromatography. 1H-NMR (400 MHz; d6-DMSO): δ 1.27 (d, 3H), 2.70 (t, 2H), 3.81 (t, 2H), 4.24 (q, 2H), 4.69 (s, 2H), 13.40 (bs, 1H).

Workup

  1. temperaturethe resulting mixture was refluxed for one hour
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. extractionextracted twice with water
  5. dry with materialThe organic layer was dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe product was purified with flash chromatography

Sources & evidence

ORD record
ord-8acc1df8a2e549dbb9e33fd7cca7f9f7
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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