Hydroxylamine → HCID 76685347, compound

HRID 2410551Notes

Reaction equation

HRID 2410551 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])=[CH:5][C:4]=1[Cl:20])#[N:2].[NH2:21][OH:22]>C(O)C>[Cl:20][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:3]=1[C:1](=[N:21][OH:22])[NH2:2])[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 66678677HCID 66678677, compound

Product 1

HCID 76685347HCID 76685347, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 2-((4-cyano-3-chlorobenzyl)(methyl)amino)acetate (1.95 g, 6.60 mmol) and 50% aqueous hydroxylamine (2.02 mL) in ethanol (10 mL) was heated at 80° C. for 5 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 to afford the title compound (2.16 g, quantitative). 1H NMR (CDCl3, 400 MHz) δ 7.48-7.42 (2H, m), 7.28 (1H, m), 4.97 (2H, s), 3.69 (2H, s), 3.18 (2H, s), 2.37 (3H, s), 1.48 (9H, 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

Sources & evidence

ORD record
ord-490b3f8f627942bba3d094beffc9ab1c
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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