Hydroxylamine → HCID 86660281, compound

HRID 1631034Notes

Reaction equation

HRID 1631034 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][N:10]([CH3:19])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:7][CH:8]=1)#[N:2].[NH2:20][OH:21]>C(O)C>[OH:21][N:20]=[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][N:10]([CH3:19])[CH2:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])=[N:7][CH:8]=1)[NH2:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86660280HCID 86660280, compound

Product 1

HCID 86660281HCID 86660281, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 2-(((5-cyanopyridin-2-yl)methyl)(methyl)amino)acetate (2.17 g; 8.31 mmol) and 50% aqueous hydroxylamine (2.50 mL; 40.8 mmol) in ethanol (40 mL) was heated at 60° C. for 2 hours. The solvent was evaporated in vacuo. The residue was partitioned between DCM and water. The organic phase was poured through a hydrophobic frit and evaporated in vacuo. The residue was triturated with ether to afford the title product as an off-white solid (1.87 g, 77%). 1H NMR (DMSO-d6, 400 MHz) δ 9.81 (1 H, s), 8.79 (1 H, d, J=2 Hz), 8.03 (1 H, dd, J=8.2, 2.2 Hz), 7.48 (1 H, d, J=8.2 Hz), 5.97 (2 H, br s), 3.80 (2 H, s), 2.32 (3 H, s), 1.46 (9 H, s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was partitioned between DCM and water
  3. additionThe organic phase was poured through a hydrophobic frit
  4. customevaporated in vacuo
  5. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-7aec4a5df46142aaa71b78b1faab873e
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

Loading…