Hydroxylamine → HCID 87332000, compound

HRID 1619144Notes

Reaction equation

HRID 1619144 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]1[CH:18]=[C:17]2[C:13]([C:14]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[C:15](=[O:19])[NH:16]2)=[CH:12][CH:11]=1.[NH2:24][OH:25].C([O-])(=O)C.[Na+]>C(O)C.O>[OH:25]/[N:24]=[C:6](/[NH2:7])\[C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[C:3]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]4([CH2:20][CH2:21][CH2:22][CH2:23]4)[C:15](=[O:19])[NH:16]3)=[CH:12][CH:11]=2)[CH:4]=1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 517045Sodium AcetateHCID 66958923HCID 66958923, compound

Product 1

HCID 87332000HCID 87332000, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A stirred mixture of 4-methyl-3-(2′-oxospiro[cyclopentane-1,3′-indoline]-6′-yl)benzonitrile (preparation 54b, 0.06 g, 0.20 mmol), hydroxylamine (0.02 g, 0.24 mmol) and sodium acetate (0.02 g, 0.27 mmol) in ethanol (0.60 mL) and water (0.10 mL) were heated to 85° C. in a sealed tube. After 6 hours, the mixture was cooled and concentrated in vacuo. Water was added to the residue and the resultant precipitate was filtered to give the title compound (0.06 g, 19%).

Workup

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additionWater was added to the residue
  4. filtrationthe resultant precipitate was filtered

Sources & evidence

ORD record
ord-8bf073a414064f5a8c992dc8797b8615
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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