Hydroxylamine → HCID 76685353, compound

HRID 2410562Notes

Reaction equation

HRID 2410562 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:5]([Cl:20])[CH:4]=1)#[N:2].[NH2:21][OH:22]>C(O)C>[Cl:20][C:5]1[CH:4]=[C:3]([C:1](=[N:21][OH:22])[NH2:2])[CH:19]=[CH:18][C:6]=1[CH2:7][N:8]([CH3:17])[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66677293HCID 66677293, compound

Product 1

HCID 76685353HCID 76685353, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 2-((4-cyano-2-chlorobenzyl)(methyl)amino)acetate (1.25 g, 4.25 mmol) and 50% aqueous hydroxylamine (1.30 mL) in ethanol (10 mL) was heated at 80° C. for 5 hours. The solvent was evaporated under vacuum. The residue was partitioned between DCM and water. The organic phase was passed through a hydrophobic frit and concentrated under vacuum to afford the title compound (1.34 g, 76%). 1H NMR (CDCl3, 400 MHz) δ 7.63 (1H, d, J=1.8 Hz), 7.59 (1H, d, J=8.0 Hz), 7.50 (1H, dd, J=8.0, 1.8 Hz), 4.84 (2H, s), 3.83 (2H, s), 3.25 (2H, s), 2.42 (3H, s), 1.48 (9H, s).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customThe residue was partitioned between DCM and water
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4d2dcfd8381b433e8fd43eb2fb928eed
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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