Hydroxylamine → HCID 21080167, compound

HRID 346483Notes

Reaction equation

HRID 346483 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([CH3:9])([CH3:8])[C:6]#[N:7].[NH2:10][OH:11].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[NH:7]=[C:6]1[C:5]([CH3:9])([CH3:8])[CH2:4][CH2:3][CH2:2][N:10]1[OH:11]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 10340Sodium CarbonateHCID 2642175-chloro-2,2-dimethylpentanenitrile

Product 1

HCID 21080167HCID 21080167, compoundYield 140.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of intermediate 8, 5-chloro-2,2-dimethylpentanenitrile, (725 mg, 5.0 mmol) and 50% aqueous NH2OH (1.0 g, 15 mmol; Aldrich) in ethanol (1.5 mL) was stirred at room temperature for 5 days, and then treated with Na2CO3 (265 mg, 2.5 mmol). The mixture was stirred at room temperature for 1 h, and concentrated in vacuo to provide 1.0 g of the title compound as crude brown oily solid. 1H NMR (DMSO-d6, 500 MHz) δ ppm: 1.29 (6H, s, Me), 1.59 (2H, m, CH2), 1.85 (2H, m, CH2), 3.62 (2H, t, J=6 Hz, NCH2); 13C NMR (CDCl3, 125.8 Hz) δ ppm: 18.23, 26.63, 33.57, 35.09, 51.85, 162.76.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30046d0099c2451c9be289019db71850
Source dataset
uspto-grants-2007_02
Patent number
US07173022B2

Reaction notes

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