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

HRID 1195779Notes

Reaction equation

HRID 1195779 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:11]([N:13]1[C:19]2=[C:20]3[C:25](=[N:26][C:27]4=[CH:28][CH:29]=[CH:30][C:17](=[C:18]24)[O:16][CH:15]([CH3:31])[C:14]1=O)[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:12]>O1CCCC1>[CH2:11]([N:13]1[C:19]2=[C:20]3[C:25](=[N:26][C:27]4=[CH:28][CH:29]=[CH:30][C:17](=[C:18]24)[O:16][CH:15]([CH3:31])[CH2:14]1)[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:12]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 543766401-ethyl-3-methyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

Product 1

HCID 542404261-Ethyl-2,3,9,10,11,12-hexahydro-3-methyl-1H-quino[4,3,2-ef][1,4]benzoxazepineYield 54.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride in tetrahydrofuran (1M, 14.22 ml) and dry tetrahydrofuran (30 ml) was added aluminum chloride (1.90 g) in portions, with stirring. After five mins, 1-ethyl-3-methyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.21 g) was added and stirring was continued for 0.5 hr. The reaction mixture was quenched with ethyl acetate (200 ml) and 10% sodium hydroxide solution (200 ml). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated. Recrystallized of the residue from diethyl ether/pentane gave 2.17 g (54%) of product, mp 101°-103° C.

Workup

  1. stirringstirring
  2. waitwas continued for 0.5 hr
  3. customThe reaction mixture was quenched with ethyl acetate (200 ml) and 10% sodium hydroxide solution (200 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customRecrystallized of the residue from diethyl ether/pentane

Sources & evidence

ORD record
ord-ca09e8cc3a964b77acf4cb0fb4626573
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

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