Sodium Hydroxide → 1,3-Dimethyl-2,3,9,10,11,12-hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepine

HRID 981932Notes

Reaction equation

HRID 981932 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][N:12]1[C:18]2=[C:19]3[C:24](=[N:25][C:26]4=[CH:27][CH:28]=[CH:29][C:16](=[C:17]24)[O:15][CH:14]([CH3:30])[C:13]1=O)[CH2:23][CH2:22][CH2:21][CH2:20]3.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:11][N:12]1[C:18]2=[C:19]3[C:24](=[N:25][C:26]4=[CH:27][CH:28]=[CH:29][C:16](=[C:17]24)[O:15][CH:14]([CH3:30])[CH2:13]1)[CH2:23][CH2:22][CH2:21][CH2:20]3

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 537292451,3-dimethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

Product 1

HCID 538317681,3-Dimethyl-2,3,9,10,11,12-hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepineYield 59%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of lithium aluminum hydride in tetrahydrofuran (1M, 10.0 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (1.86 g) in portions, with stirring. The reaction mixture was stirred for five mins and 1,3-dimethyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (3.95 g) was added. After stirring for 30 min, ethyl acetate (200 ml) and 10% sodium hydroxide solution (200 ml) were added, and the organic layer was separated, dried over anhydrous magnesium sulfate and concentrated. Recrystallization of the residue from diethyl ether/pentane gave 2.2 g (59%) of product, mp 125°-126.5° C.

Workup

  1. stirringThe reaction mixture was stirred for five mins
  2. stirringAfter stirring for 30 min
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customRecrystallization of the residue from diethyl ether/pentane

Sources & evidence

ORD record
ord-26114fa7dfff41c0b74cb8c976499837
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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