Hydroxyamine hydrochloride → HCID 178513273, compound

HRID 2192461Notes

Reaction equation

HRID 2192461 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.Cl.[NH2:14][OH:15].C(=O)(O)[O-].[Na+]>C(O)C>[OH:15][NH:14][C:11]([C:6]1[C:5]2[CH:4]=[CH:3][N:2]=[CH:1][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[NH:12]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 459770Isoquinoline-5-carbonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 178513273HCID 178513273, compoundYield 119.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

5-Isoquinolinecarbonitrile (2 g, 13 mmol; available from Fulcrum Scientific Product List), hydroxylamine.hydrochloride (7.21 g, 104 mmol) and sodium bicarbonate (10.9 g, 130 mmol), were added to a 0.5 L round bottomed flask containing ethanol (250 ml). The reaction mixture was heated at 65° C. for 3 hours and stirred for 12 hours. The cooled reaction mixture was evaporated to a smaller volume under reduced pressure and chromatographed over a 4×6 inch silica column eluting with ethanol to provide the title compound as a yellow solid (2.9 g).

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated to a smaller volume under reduced pressure
  3. customchromatographed over a 4×6 inch silica column
  4. washeluting with ethanol

Sources & evidence

ORD record
ord-ec217c3793d643ec9aded3017603a857
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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