Hydroxylamine → HCID 178510734, compound

HRID 2169300Notes

Reaction equation

HRID 2169300 reaction equation
[C:1]1([C:7]2([CH2:17][C:18]#[N:19])[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:20][OH:21].C(OCC)(=O)C.CCCCCC>C(O)C>[OH:21][NH:20][C:18](=[NH:19])[CH2:17][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9][C:10]2([O:11][CH2:12][CH2:13][O:14]2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 8058HexaneHCID 8857Ethyl AcetateHCID 86725946(8-Phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)-acetonitrile

Product 1

HCID 178510734HCID 178510734, compoundYield 50.22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 8-phenyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (264) (1.5 g, 5.83 mmol) in ethanol (30 mL) was added NH2OH (50% aqueous solution, 1.1 mL, 17.49 mmol) and the reaction mixture was heated at 60° C. for 16 h. Silica thin layer chromatography was performed (ethyl acetate:Hexane=1:1, Rf=0.15). The reaction mixture was concentrated in vacuo to yield a crude mixture which was triturated with diethyl ether to obtain pure N-hydroxy-2-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)-acetamidine (266) (850 mg, 50.22%) as an off-white solid which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto yield a crude mixture which
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-71daaf835c8849558167abb53909a2d8
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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