Sodium Hydroxide → 3-cyclopentyl-5-Isoxazolamine

HRID 1930358Notes

Reaction equation

HRID 1930358 reaction equation
Cl.[NH2:2][OH:3].[CH:4]1([C:9](=O)[CH2:10][C:11]#[N:12])[CH2:8][CH2:7][CH2:6][CH2:5]1.[OH-].[Na+]>O>[CH:4]1([C:9]2[CH:10]=[C:11]([NH2:12])[O:3][N:2]=2)[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 135921183-Cyclopentyl-3-oxopropanenitrile

Product 1

HCID 133773103-cyclopentyl-5-IsoxazolamineYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Hydroxylamine hydrochloride (6 g, 86 mmol) and 3-cyclopentyl-3-oxopropanenitrile (10 g, 73 mmol) were added to a solution of NaOH (9 g, 225 mmol) in water (100 mL) and the resulting mixture was heated at 50° C. overnight. The precipitate was collected by filtration, washed with water, and dried to give 3-cyclopentylisoxazol-5-amine (6.7 g, 61% yield). 1H NMR (400 MHz, DMSO-d6): δ 6A3 (s, 2 H), 4.77 (s, 1 H), 2.84 (m, 1 H), 1.87-1.51(m, 8 H); MS (ESI) m/z: 153.1 (M+H+).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-0b2cf7c8dfc144cdae201c5ad858b08a
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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