Sodium Hydroxide → HCID 54402947, compound

HRID 981942Notes

Reaction equation

HRID 981942 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[C:11]1([CH:17]2[C:23](=O)[NH:22][C:21]3=[C:25]4[C:30](=[N:31][C:32]5=[CH:33][CH:34]=[CH:35][C:19](=[C:20]35)[O:18]2)[CH2:29][CH2:28][CH2:27][CH2:26]4)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>O1CCCC1>[C:11]1([CH:17]2[CH2:23][NH:22][C:21]3=[C:25]4[C:30](=[N:31][C:32]5=[CH:33][CH:34]=[CH:35][C:19](=[C:20]35)[O:18]2)[CH2:29][CH2:28][CH2:27][CH2:26]4)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 545386111,3,9,10,11,12-Hexahydro-3-phenyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one

Product 1

HCID 54402947HCID 54402947, compoundYield 67.72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride in tetrahydrofuran (1M, 12.0 ml) was added to dry tetrahydrofuran (30 ml) followed by aluminum chloride (1.60 g). The mixture was stirred for 15 mins and 1,3,9,10,11,12-hexahydro-3-phenyl-2H-quino[4,3,2-ef][1,4]benzoxazepine-2-one (3.30 g) was added, with stirring. After 30 mins, 10% sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was purified by flash chromatography (5% triethylamine-ethyl acetate). Evaporation of the appropriate fractions followed by recrystallization of the residue from dichloromethane-pentane gave 2.14 g (67.72%) of product, mp 194°-195° C.

Workup

  1. stirringwith stirring
  2. waitAfter 30 mins
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (5% triethylamine-ethyl acetate)
  8. customEvaporation of the appropriate fractions
  9. customfollowed by recrystallization of the residue from dichloromethane-pentane

Sources & evidence

ORD record
ord-f677cfd654374540a2ea88744e104638
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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