Hydroxyamine hydrochloride → HCID 86649545, compound

HRID 474906Notes

Reaction equation

HRID 474906 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[Br:9][C:10]1[CH:22]=[C:21]2[C:13]([C:14]3[C:15](=O)[CH2:16][CH2:17][CH2:18][C:19]=3[N:20]2[CH3:23])=[CH:12][CH:11]=1>CCO.O>[Br:9][C:10]1[CH:22]=[C:21]2[C:13]([C:14]3[C:15](=[N:2][OH:3])[CH2:16][CH2:17][CH2:18][C:19]=3[N:20]2[CH3:23])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 58093405HCID 58093405, compound

Product 1

HCID 86649545HCID 86649545, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Hydroxylamine hydrochloride (3.21 g, 46.5 mmol) and sodium acetate (3.81 g, 46.5 mmol) were added to a suspension of 7-bromo-9-methyl-2,3-dihydro-1H-carbazol-4(9H)-one (8.61 g, 30.9 mmol) in EtOH (79.0 mL) and H2O (27.0 mL), and the resulting suspension was heated at reflux for 20 h. The reaction was cooled to ˜40° C., and the solids were collected by filtration. The solids were washed with H2O and EtOH. The solids were divided into two batches of 3.93 g and 4.08 g and recrystallized in CH3CN (500 mL per batch). The material was allowed to crystallize for two days the resulting crystals were collected by filtration to afford the title compound (6.31 g, 70%) as an off-white crystalline solid: 1H NMR (500 MHz, DMSO-d6) δ 10.33 (s, 1H), 7.82 (d, J=8.5 Hz, 1H), 7.70 (d, J=2.0 Hz, 1H), 7.20 (dd, J=8.0, 1.5 Hz, 1H), 3.66 (s, 3H), 2.81 (t, J=6.0 Hz, 2H), 2.66 (t, J=6.0 Hz, 2H), 1.94-1.91 (m, 2H). Additional material was obtained by concentrating the filtrate to 200 mL and collecting the resulting solids to afford the title compound (1.22 g, 13%) as an off-white powder.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 20 h
  3. filtrationthe solids were collected by filtration
  4. washThe solids were washed with H2O and EtOH
  5. customrecrystallized in CH3CN (500 mL per batch)
  6. customto crystallize for two days the resulting crystals
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-d1185807119140ca8ee5c75e19d9b59f
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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