Sodium Hydroxide → HCID 67756675, compound

HRID 981944Notes

Reaction equation

HRID 981944 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]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:13]1=O)[CH2:23][CH2:22][CH2:21][CH2:20]3.[OH-].[Na+].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43]>O1CCCC1>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[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]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:13]1)[CH2:23][CH2:22][CH2:21][CH2:20]3

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 54394200HCID 54394200, compound

Product 1

HCID 67756675HCID 67756675, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride in tetrahydrofuran (1M, 14.0 ml) was added to dry tetrahydrofuran (30 ml) followed by aluminum chloride (1.86 g). The mixture was stirred for 15 mins and 1,3,9,10,11,12-hexahydro-1-methyl-3-phenyl-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.00 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 the filtrate was evaporated. The residue was purified by flash chromatography (5% triethylamine-ethyl acetate). The residue, obtained by evaporation of the appropriate fractions, was treated with fumaric acid in methanol-ether. The solid was collected and recrystallized from methanol-ether to give 4.05 g (56.7%) of product, m.p. 172°-173° 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. customthe filtrate was evaporated
  7. customThe residue was purified by flash chromatography (5% triethylamine-ethyl acetate)
  8. customThe residue, obtained by evaporation of the appropriate fractions
  9. customThe solid was collected
  10. customrecrystallized from methanol-ether

Sources & evidence

ORD record
ord-b1e1767622714505be03b2fc82368a1c
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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