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

HRID 981930Notes

Reaction equation

HRID 981930 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:11][CH:12]1[C:18](=O)[NH:17][C:16]2=[C:20]3[C:25](=[N:26][C:27]4=[CH:28][CH:29]=[CH:30][C:14](=[C:15]24)[O:13]1)[CH2:24][CH2:23][CH2:22][CH2:21]3.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:11][CH:12]1[CH2:18][NH:17][C:16]2=[C:20]3[C:25](=[N:26][C:27]4=[CH:28][CH:29]=[CH:30][C:14](=[C:15]24)[O:13]1)[CH2:24][CH2:23][CH2:22][CH2:21]3

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 541566201,3,9,10,11,12-Hexahydro-3-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

Product 1

HCID 542146222,3,9,10,11,12-Hexahydro-3-methyl-1H-quino[4,3,2-ef][1,4]benzoxazepineYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of lithium aluminum hydride in tetrahydrofuran (1M, 15.82 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (2.10 g) in portions; with stirring. After 5 mins, 1,3,9,10,11,12-hexahydro-3-methyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.24) was added, and the reaction mixture was stirred at room temperature for four hrs. Ethyl acetate (200 ml) and 10% sodium hydroxide solution (200 ml) were added. The organic phase was separated, dried over anhydrous magnesium sulfate, and concentrated. The residue was adhered to silica and flash chromatographed (5% triethylamine/toluene. The appropriate fractions were concentrated and the residue was triturated with diethyl ether to yield 2.48 g (62%) of product, mp 169°-170.5° C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for four hrs
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customchromatographed (5% triethylamine/toluene
  6. concentrationThe appropriate fractions were concentrated
  7. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-9d668eb0464849dfae5b0bd64d3f593c
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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