Hydroxylamine → HCID 11404963, compound

HRID 1986356Notes

Reaction equation

HRID 1986356 reaction equation
[NH2:1][C:2]1[C:3]([NH:23][CH2:24][CH3:25])=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([NH:15]C(=O)OC(C)(C)C)[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.[C:26]([CH2:28][C:29](OCC)=O)#[N:27].[N:34]([O-:36])=O.[Na+].[OH-].[Na+].[NH2:40]O>CO.Cl.O>[NH2:15][C:11]1[CH:10]=[C:9]([O:8][C:5]2[N:6]=[CH:7][C:2]3[N:1]=[C:29]([C:28]4[C:26]([NH2:40])=[N:27][O:36][N:34]=4)[N:23]([CH2:24][CH3:25])[C:3]=3[CH:4]=2)[CH:14]=[CH:13][CH:12]=1

Participants

9

Reactant 5

HCID 787HydroxylamineHCID 7764Ethyl cyanoacetateHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 86623345HCID 86623345, compound

Product 1

HCID 11404963HCID 11404963, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The product from Step 3 (0.81 g, 2.3 mmol) and ethyl cyanoacetate (0.52 g, 4.6 mmol) were heated together at 195° C. for 25 minutes. After cooling the mixture to rt, the residue was dissolved in methanol (0.8 mL) and 5N hydrochloric acid (3 mL). The resulting mixture was treated portionwise with sodium nitrite (0.32 g, 4.6 mmol) and stirred at room temperature for 90 minutes. The pH of the mixture was adjusted to 11 by addition of 50% sodium hydroxide solution and a 50% solution of hydroxylamine in water (1.6 mL) was added. The mixture was heated at 110° C. for 16 h and the reaction allowed to cool to rt. The mixture was partitioned between ethyl acetate and water, then the organic phase was washed with brine and evaporated in vacuo. The residue was purified by HPLC to afford the title compound (0.12 g, 15%). MS (ES+) m/e 338 [M+H]+.

Workup

  1. temperatureThe mixture was heated at 110° C. for 16 h
  2. temperatureto cool to rt
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washthe organic phase was washed with brine
  5. customevaporated in vacuo
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-106bb874fa2848b3bfab80c848e8b8d6
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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