Hydroxylamine → HCID 133681488, compound

HRID 2203311Notes

Reaction equation

HRID 2203311 reaction equation
[CH3:1][CH:2]([C:8]#[N:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:10][OH:11]>CO>[NH2:9]/[C:8](=[N:10]\[OH:11])/[CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 98018Ethyl 2-cyanopropionate

Product 1

HCID 133681488HCID 133681488, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-methylcyanoacetate (5 g, 39 mmol) and hydroxylamine (2.6 g, 39 mmol) were dissolved in 50 mL of MeOH. The solution was heated at the 50° C. overnight. The solution was then concentrated and the residue purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR δ (ppm) (DMSO-d6): 9.05 (1H, s), 5.40 (2H, s), 4.06 (2H, dd, J=12.8, 7.0 Hz), 3.15 (1H, m), 1.24 (3H, d, J=7.2 Hz), 1.18 (3H, t, J=7.1 Hz). m/z=161.1 (M+H)

Workup

  1. concentrationThe solution was then concentrated
  2. customthe residue purified by silica gel chromatography
  3. customto give the indicated product

Sources & evidence

ORD record
ord-f7d590db05bb4515859da1a703ef0b5a
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

Loading…