Hydroxylamine → HCID 67324353, compound

HRID 1397387Notes

Reaction equation

HRID 1397387 reaction equation
[CH:1]([C:3]1[O:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1)=O.[NH2:13]O.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CO.CN(C=O)C>[C:1]([C:3]1[O:4][CH:5]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1)#[N:13]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 111923Propylphosphonic anhydrideHCID 10583255Ethyl 2-formyl-1,3-oxazole-4-carboxylate

Product 1

HCID 67324353HCID 67324353, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2-formyloxazole-4-carboxylate (650 mg, 3.84 mmol) in methanol (25 mL) was cooled to 0° C. and 50% aqueous hydroxylamine (0.22 mL, 7.68 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 3 h. Solvent was removed under reduced pressure and the crude product (0.52 g) obtained was dissolved in DMF (20 mL). T3P (3.4 mL, 5.65 mmol; 50% in EtOAc) was added to the reaction mixture and heated to 100° C. for 2 h. The reaction mixture was quenched with saturated NaHCO3 solution and the organic product was extracted with EtOAc. Solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10% EtOAc in petroleum ether) to afford ethyl 2-cyanooxazole-4-carboxylate (0.34 g, yield 53%) as an off white solid. 1H NMR (300 MHz, CDCl3) δ 8.39 (s, 1H), 4.48-4.41 (q, J=7.0 Hz, 2H), 1.44-1.39 (t, J=7.0 Hz, 3H).

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe crude product (0.52 g) obtained
  3. temperatureheated to 100° C. for 2 h
  4. customThe reaction mixture was quenched with saturated NaHCO3 solution
  5. extractionthe organic product was extracted with EtOAc
  6. customSolvent was removed under reduced pressure
  7. customthe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-14be85a766c04027861618f6fb027a45
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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