Potassium Sodium Tartrate → HCID 67763856, compound

HRID 362888Notes

Reaction equation

HRID 362888 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:11][C:12]1[CH:28]=[CH:27][C:15]2[O:16][CH2:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[CH:20]([C:21]#[N:22])[C:14]=2[CH:13]=1.[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>CCOCC.O>[NH2:22][CH2:21][CH:20]1[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[CH2:17][O:16][C:15]2[CH:27]=[CH:28][C:12]([Br:11])=[CH:13][C:14]1=2

Participants

8

Reactant 5

HCID 9357Potassium Sodium TartrateHCID 166653HydrideHCID 6451240Aluminum(III) ChlorideHCID 10424856HCID 10424856, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 67763856HCID 67763856, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent4×

Procedure

A solution of AlCl3 (1.0 g, 7.5 mmol) in dry ether (10 ml) was added rapidly to a solution of LiAlH4 (0.5 g, 13.2 mmol) in dry ether (13 ml). After 5 minutes, a suspension of 2-bromo-11-cyano-6,11-dihydrodibenz[b,e]oxepin (2.0 g, 6.7 mmol) in dry ether (100 ml) was added to the mixture of hydride. The reaction mixture was stirred for 4.5 hours. Water and Rochelle Salt were added to the reaction mixture. The mixture was poured into ether. The organic layer was dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel to give 11-aminomethyl-2-bromo-6,11-dihydrodibenz[b,e]oxepin (48.9%).

Workup

  1. dry with materialThe organic layer was dried (MgSO4)
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-48580e43b49647cebd308404d18d2cea
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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