Sodium Hydroxide → 8-Methoxy-2,3,4,5-tetrahydro-1H-benzo(c)azepine

HRID 412594Notes

Reaction equation

HRID 412594 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:18][CH2:17][CH2:16][NH:15][C:14](=O)[C:13]=2[CH:20]=1.[OH-].[Na+]>O1CCCC1.O1CCOCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][C:13]=2[CH:20]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 112755298-Methoxy-2,3,4,5-tetrahydro-benzo[c]azepin-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 154969548-Methoxy-2,3,4,5-tetrahydro-1H-benzo(c)azepineYield 98.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of lithium aluminum hydride (3.07 g) in tetrahydrofuran (60 ml) was dropwise added a solution of 8-methoxy-2,3,4,5-tetrahydrobenz[c]azepin-1-one (4.42 g) in 1,4-dioxane (30 ml) with ice-cooling and the mixture was refluxed for 20 hours. After completion of the reaction, 20% aqueous sodium hydroxide solution was added dropwise with ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was filtrated, and the solvent was evaporated and the residue was dried under reduced pressure to give the title compound (4.05 g).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed for 20 hours
  3. additionwas added dropwise with ice-
  4. temperaturecooling
  5. customAfter completion of the reaction
  6. filtrationthe reaction mixture was filtrated
  7. customthe solvent was evaporated
  8. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-b7ee8df23e1f4a1b87923caa18e30898
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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