Hydroxyamine hydrochloride → HCID 16226366, compound

HRID 2219814Notes

Reaction equation

HRID 2219814 reaction equation
[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]([CH3:16])[C:14]([C:17]#[N:18])=[CH:13][CH:12]=3)[CH:9]=2)[C:4](=O)[CH2:3]1.C([O-])(=O)C.[Na+].Cl.[NH2:27][OH:28]>C(O)C.O>[OH:28]/[N:27]=[C:4]1\[CH2:3][C:2]([CH3:20])([CH3:1])[C:10]2[C:5]\1=[CH:6][CH:7]=[C:8]([C:11]1[N:15]([CH3:16])[C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)[CH:9]=2

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 16004661HCID 16004661, compound

Product 1

HCID 16226366HCID 16226366, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred mixture of 5-(3,3-dimethyl-1-oxo-2,3-dihydro-1H-inden-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (0.07 g, 0.26 mmol) in ethanol (1.6 mL)/water (0.4 mL) was added sodium acetate (0.03 g, 0.34 mmol) and hydroxylamine hydrochloride (0.02 g, 0.32 mmol). The resulting mixture was heated to reflux for 5 hours. The solution was allowed to cool to room temperature, diluted with water, and filtered to give 5-[(1E)-1-(hydroxyimino)-3,3-dimethyl-2,3-dihydro-1H-inden-5-yl]-1-methyl-1H-pyrrole-2-carbonitrile as a white solid (0.04 g, 55%). MS (ES) m/z 280.1. HRMS: calcd for C17H17N3O+H+, 280.14444; found (ESI, [M+H]+), 280.145.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 5 hours
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d0f3ad9f6da040ccb3d82d4dfee9f368
Source dataset
uspto-grants-2008_08
Patent number
US07414142B2

Reaction notes

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