Hydroxylamine → HCID 67324353, compound

HRID 646894Notes

Reaction equation

HRID 646894 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH:11]=O)[O:9][CH:10]=1)=[O:5])[CH3:2].[NH2:13]O>CO>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]#[N:13])[O:9][CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

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

Product 1

HCID 67324353HCID 67324353, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-formyl-oxazole-4-carboxylic acid ethyl ester (Panek et al. J. Org. Chem., 6496, (1996)) (171 mg, 1.11 mmol) in MeOH (3 mL) was added NH2OH (50% wt. H2O, 161 μL, 2.4 mmol). The reaction was allowed to stir for 2 h, and then concentrated in vacuo. The crude oxime was treated with acetic anhydride (4 mL) and heated with stirring at 150° C. for 24 h. The acetic anhydride was removed under vacuo, and the crude material was purified by preparative thin layer chromatography (60% ether-hexanes) to afford 56 mg (31%) of the title compound as an off-white solid. 1H-NMR (CDCl3; 400 MHz): δ 8.40 (s, 1H), 4.46 (q, 2H, J=7.1 Hz), 1.43 (t, 3H, J=7.1 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe crude oxime was treated with acetic anhydride (4 mL)
  3. temperatureheated
  4. stirringwith stirring at 150° C. for 24 h
  5. customThe acetic anhydride was removed under vacuo
  6. customthe crude material was purified by preparative thin layer chromatography (60% ether-hexanes)

Sources & evidence

ORD record
ord-6afa02ecd3c74ebaab308e7281631714
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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