Hydroxyamine hydrochloride → ethyl 3-[5-[(Z)-N'-hydroxycarbamimidoyl]indol-1-yl]propanoate

HRID 423332Notes

Reaction equation

HRID 423332 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])[CH: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])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 59318415Ethyl 3-(5-cyano-1H-indol-1-yl)propanoate

Product 1

HCID 178471832ethyl 3-[5-[(Z)-N'-hydroxycarbamimidoyl]indol-1-yl]propanoateYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 3-(5-cyano-1H-indol-1-yl)propanoate (D51) (1.7 g, 7.2 mmol), hydroxylamine hydrochloride (1.0 g, 14.4 mmol) and sodium hydrogen carbonate (2.42 g, 28.9 mmol) were suspended in ethanol (100 ml) and stirred at 50° C. for 3 days. A single product formed but 15% starting material remained. Cooled, filtered off the inorganic material and evaporated off the solvent. The product was crystallised from a mixture of EtOAc, diethyl ether and hexane to yield 1.9 g of the title compound as a white solid. MS (ES) C14H17N3O3 requires 275; found 276. (MH+).

Workup

  1. customA single product formed
  2. temperatureCooled
  3. filtrationfiltered off the inorganic material
  4. customevaporated off the solvent
  5. customThe product was crystallised from a mixture of EtOAc, diethyl ether and hexane

Sources & evidence

ORD record
ord-23eb158416564a80a2aef4c48ed5518f
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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