Hydroxyamine hydrochloride → HCID 178471847, compound

HRID 2189780Notes

Reaction equation

HRID 2189780 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:7]=[CH:6]2)#[N:2].C(=O)(O)[O-].[Na+].Cl.[NH2:25][OH:26]>C(O)C>[OH:26][NH:25][C:1](=[NH:2])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:7]=[CH:6]2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 59316705Ethyl 3-(5-cyano-1H-indazol-1-yl)propanoate

Product 1

HCID 178471847HCID 178471847, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 3-(5-cyano-1H-indazol-1-yl)propanoate (D47) (1 g, 4.11 mmol) was dissolved in ethanol (30 ml) and sodium bicarbonate (1.73 g, 20.88 mmol) and hydroxylamine hydrochloride (571 mg, 8.22 mmol) were added. The reaction was left at room temperature overnight and then heated to 50° C. for 4 hours then left to cool overnight. The reaction mixture was filtered and the residue washed with ethanol. The ethanolic filtrate was evaporated to dryness in vacuo and then triturated with ether to give the title compound (764 mg) as a white solid of approximately 90% purity. MS (ES): C13H16N4O3 requires 276; found (MH+) 277.

Workup

  1. waitthen left
  2. temperatureto cool overnight
  3. filtrationThe reaction mixture was filtered
  4. washthe residue washed with ethanol
  5. customThe ethanolic filtrate was evaporated to dryness in vacuo
  6. customtriturated with ether

Sources & evidence

ORD record
ord-a5111fba89db4246940d52fb00a03d7a
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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