Hydroxyamine hydrochloride → HCID 178471847, compound

HRID 2189782Notes

Reaction equation

HRID 2189782 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].Cl.[NH2:20][OH:21].C(=O)(O)[O-].[Na+]>C(O)C>[OH:21][NH:20][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, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3-(5-cyano-1H-indazol-1-yl)propanoate D47 (3.6 g, 14.80 mmol) was dissolved in ethanol (40 ml), hydroxylamine hydrochloride (2.057 g, 29.6 mmol) and sodium bicarbonate (6.22 g, 74.0 mmol) were added. The mixture was heated at 60° C. overnight. Cooled, filtered and the filtrate was evaporated, dissolved in EtOAc, washed with water (3×20 ml), dried over MgSO4 and evaporated again to give (1.75 g) of product. A further 0.290 g of white crystals were recovered from the rotary evaporater. MS (ES+): C13H16N4O3 requires 276; found (MH+) 277.

Workup

  1. temperatureCooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. dissolutiondissolved in EtOAc
  5. washwashed with water (3×20 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated again

Sources & evidence

ORD record
ord-fc2641e7012e44fab4db1cdf1733347d
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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