Hydroxyamine hydrochloride → HCID 87186719, compound

HRID 474988Notes

Reaction equation

HRID 474988 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[C:21]3[C:20](=O)[CH2:19][CH2:18][CH2:17][C:16]=3[N:15]([CH3:23])[C:14]=2[N:24]=1>CCO.O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[C:21]3[C:20](=[N:2][OH:3])[CH2:19][CH2:18][CH2:17][C:16]=3[N:15]([CH3:23])[C:14]=2[N:24]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 58093447HCID 58093447, compound

Product 1

HCID 87186719HCID 87186719, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (0.54 g, 7.9 mmol) and sodium acetate (0.65 g, 7.9 mmol) were added to a suspension of 2-bromo-9-methyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]indol-5-one (1.5 g, 5.3 mmol) in EtOH (13 mL) and H2O (5 mL), and the resulting suspension was heated at reflux for 4 h. The reaction was cooled to ambient temperature, and the solids were collected by filtration. The solids were washed with EtOH to provide the title compound (1.34 g, 87%) as an off-white powder: 1H NMR (500 MHz, DMSO-d6) δ 10.49 (s, 1H), 8.05 (d, J=8.0 Hz, 1H), 7.31 (d, J=8.0 Hz, 1H), 3.68 (s, 3H), 2.86 (t, J=6.0 Hz, 2H), 2.68 (t, J=8.0 Hz, 2H), 1.96-1.84 (m, 2H).

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 4 h
  3. filtrationthe solids were collected by filtration
  4. washThe solids were washed with EtOH

Sources & evidence

ORD record
ord-4068b0a1fcd241e49346fb0fa3a46af9
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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