Hydroxylamine → HCID 57554625, compound

HRID 1511883Notes

Reaction equation

HRID 1511883 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[C:5]2([CH2:11][CH2:10][C@H:9]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[CH2:8]2)[NH:4][C:3]1=[O:20].[NH2:21][OH:22]>C(O)C.O>[OH:22]/[N:21]=[C:16](\[NH2:17])/[C:15]1[CH:18]=[CH:19][C:12]([C@H:9]2[CH2:10][CH2:11][C:5]3([NH:4][C:3](=[O:20])[N:2]([CH3:1])[C:6]3=[O:7])[CH2:8]2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 57554620HCID 57554620, compound

Product 1

HCID 57554625HCID 57554625, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-((7S)-3-methyl-2,4-dioxo-1,3-diazaspiro[4.4]nonan-7-yl)benzonitrile (0.88 g, 3.27 mmol) was suspended in ethanol (20 ml). To this was added hydroxylamine (0.240 ml, 3.59 mmol) as 50% weight solution in water, and the reaction was heated to 60° C. under an atmosphere of nitrogen for about 20 hours. The reaction mixture was left to cool down to ambient temperature. Solvent was partially removed. The resulting white precipitate was filtered, rinsed with cold ethanol and vacuum-dried to afford (Z)-N′-hydroxy-4-{(7S)-3-methyl-2,4-dioxo-1,3-diazaspiro[4.4]nonan-7-yl}benzimidamide as light brown solid (1.12 g, 3.20 mmol).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool down to ambient temperature
  3. customSolvent was partially removed
  4. filtrationThe resulting white precipitate was filtered
  5. washrinsed with cold ethanol
  6. customvacuum-dried

Sources & evidence

ORD record
ord-a18755522aa9414ca0e4bc8e0f7dd267
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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