Water → HCID 59389605, compound

HRID 2357959Notes

Reaction equation

HRID 2357959 reaction equation
O1[CH2:6][CH2:5][CH:4]([C:7]#[N:8])[CH2:3]C1.Cl.[CH3:10][NH:11][OH:12].[C:13](=[O:16])([O-])[O-].[Na+].[Na+].O>CCO.O>[OH:12][N:11]([CH3:10])[C:7]([CH:4]1[CH2:3][CH2:13][O:16][CH2:6][CH2:5]1)=[NH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 77906N-methylhydroxylamine hydrochlorideHCID 11815837Oxane-4-carbonitrile

Product 1

HCID 59389605HCID 59389605, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of tetrahydro-2H-pyran-4-carbonitrile (1.0 g, 9.0 mmol), N-methyl hydroxylamine hydrochloride (1.13 g, 13.5 mmol) in EtOH/H2O (1:1, 20 mL) was added sodium carbonate (0.71 g, 6.75 mmol) and H2O (10 mL) to dissolve. The mixture as stirred at 100° C. for 3 h then cooled and concentrated. The residue was triturated with 10% MeOH/CH2Cl2. The mixture was filtered to give the title compound as a white solid (0.92 g, 65% yield). 1H NMR (300 MHz, CDCl3) δ: 4.05 (2H, dd, J=11.2, 3.5 Hz), 3.54 (3H, s), 3.44 (2H, td, J=11.8, 12.3 Hz), 2.48-2.74 (1H, m), 1.83-1.69 (4H, m). LCMS (M+H) calcd for C7H15N2O2: 159.11; found: 159.07.

Workup

  1. dissolutionto dissolve
  2. temperaturethen cooled
  3. concentrationconcentrated
  4. customThe residue was triturated with 10% MeOH/CH2Cl2
  5. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-58a9399edfa04614ae8bae4f7321ef94
Source dataset
uspto-grants-2010_07
Patent number
US07763630B2

Reaction notes

Loading…