Hydroxyamine hydrochloride → HCID 178513275, compound

HRID 2192493Notes

Reaction equation

HRID 2192493 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[O:9]=[C:10]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20]#[N:21])[C:14]=2[CH:13]=[CH:12][NH:11]1>C(O)C>[OH:3][NH:2][C:20]([C:15]1[C:14]2[CH:13]=[CH:12][NH:11][C:10](=[O:9])[C:19]=2[CH:18]=[CH:17][CH:16]=1)=[NH:21]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 426091831-Oxo-1,2-dihydroisoquinoline-5-carbonitrile

Product 1

HCID 178513275HCID 178513275, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (3.18 g) and sodium bicarbonate (5.7 g) were added to a suspension of 1-oxo-1,2-dihydro-5-isoquinolinecarbonitrile (Journal of Organic Chemistry (1964), 29(9), 2534-42; 3.9 g) in ethanol (600 ml) at room temperature. The reaction mixture was heated to reflux and stirred for 48 hours. After cooling, the suspension was filtered. The solid was collected, washed with water (2×100 ml) and ethanol (100 ml) to give the title compound (2.75 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. filtrationthe suspension was filtered
  5. customThe solid was collected
  6. washwashed with water (2×100 ml) and ethanol (100 ml)

Sources & evidence

ORD record
ord-fdad223c43334a5d93f66e98a2941661
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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