Hydroxyamine hydrochloride → HCID 76664802, compound

HRID 474897Notes

Reaction equation

HRID 474897 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[CH2:15][CH2:16][CH2:17][C:18](=O)[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[CH2:15][CH2:16][CH2:17][C:18](=[N:2][OH:3])[C:19]=3[N:20]2[CH3:23])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 58093399HCID 58093399, compound

Product 1

HCID 76664802HCID 76664802, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (0.56 g, 8.1 mmol) and sodium acetate (0.66 g, 8.1 mmol) were added to a suspension of 7-bromo-9-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one (1.5 g, 5.4 mmol) in EtOH (14 mL) and H2O (5.0 mL), and the resulting suspension was heated at reflux for 18 h. The reaction was cooled and concentrated to dryness. The resulting solid was triturated with MeOH (100 mL), and the solids were dried to yield the title compound (1.4 g, 90%) as an off-white powder: 1H NMR (300 MHz, DMSO-d6) δ 11.14 (s, 1H), 7.66 (s, 1H), 7.47 (d, J=8.5 Hz, 1H), 7.15 (dd, J=8.5, 1.0 Hz, 1H), 3.95 (s, 3H), 2.79-2.72 (m, 4H), 1.88-1.83 (m, 2H).

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 18 h
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated to dryness
  5. customThe resulting solid was triturated with MeOH (100 mL)
  6. customthe solids were dried

Sources & evidence

ORD record
ord-43fc116e85b642fc8887d66522e782de
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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