Aluminum(III) Chloride → 2,3,9,10,11,12-Hexahydro-1-methyl-1H-quino-[4,3,2-ef][1,4]benzoxazepine

HRID 981924Notes

Reaction equation

HRID 981924 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][CH2:14][C:13]1=O)[CH2:23][CH2:22][CH2:21][CH2:20]3>O1CCCC1>[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][CH2:14][CH2:13]1)[CH2:23][CH2:22][CH2:21][CH2:20]3

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 53993904HCID 53993904, compound

Product 1

HCID 538157592,3,9,10,11,12-Hexahydro-1-methyl-1H-quino-[4,3,2-ef][1,4]benzoxazepineYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride in tetrahydrofuran (1.0M, 15.82 ml) and dry tetrahydrofuran (32 ml) was added aluminum chloride (2.10 g) in portions. The mixture was stirred for five mins, 1,3,9,10,11,12-hexahydro-1-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.24 g) was added and the mixture was stirred at room temperature overnight. The reaction mixture was quenched with ethyl acetate (150 ml), 10% sodium hydroxide solution was added, and the organic layer was separated. The organic layer was washed wit brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was adhered to silica (methanol) and flash chromatographed (30-50% ethyl acetate/Hexane) to yield 3.61 g (89.6%) of product, mp 97°-98° C.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction mixture was quenched with ethyl acetate (150 ml), 10% sodium hydroxide solution
  3. additionwas added
  4. customthe organic layer was separated
  5. washThe organic layer was washed wit brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (30-50% ethyl acetate/Hexane)

Sources & evidence

ORD record
ord-94fe0a35152d482ead283c5def26da81
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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