Hydroxylamine → 5-Isoxazolamine,3-cyclohexyl-(9CI)

HRID 1241600Notes

Reaction equation

HRID 1241600 reaction equation
[CH:1]1([C:7](=O)[CH2:8][C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:12][OH:13]>CCO>[NH2:10][C:9]1[O:13][N:12]=[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 113095973-Cyclohexyl-3-oxopropanenitrile

Product 1

HCID 133773115-Isoxazolamine,3-cyclohexyl-(9CI)

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3-cyclohexyl-3-oxopropanenitrile (1 g, 6.6 mmol, Step A) in EtOH (1 mL) at RT was added hydroxylamine (0.81 mL, 50% in H2O). The reaction was stirred 12 h at RT. The solid was filtered off, washed with 1N NaOH, then H2O and dried over P2O5 to give 5-amino-3-cyclohexylisoxazole.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with 1N NaOH
  3. dry with materialH2O and dried over P2O5

Sources & evidence

ORD record
ord-c5eaab0ff9c64f61b599702c5654a6ee
Source dataset
uspto-grants-2006_10
Patent number
US07115617B2

Reaction notes

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