Lithium Carbonate → 8-Chloro-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol

HRID 1279701Notes

Reaction equation

HRID 1279701 reaction equation
[Cl:1][C:2]1(Cl)[C:14](=[O:15])[C:13]2[C:12]3[C:7]4=[C:8]([O:16][CH2:17][CH:18]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[N:6]4[C:5]=2[CH2:4][CH2:3]1)[CH:9]=[CH:10][CH:11]=3.C(=O)([O-])[O-].[Li+].[Li+].[Cl-].[Li+]>CN(C=O)C>[Cl:1][C:2]1[C:14]([OH:15])=[C:13]2[C:5]([N:6]3[CH:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:17][O:16][C:8]4[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]3=4)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11125Lithium CarbonateHCID 433294Lithium ChlorideHCID 121486298,8-dichloro-1-phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-one

Product 1

HCID 121486308-Chloro-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-olYield 78.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 8,8-dichloro-1-phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-one (0.4072 g, 1.09 mmol) in DMF (5 mL) is added lithium carbonate (0.242 g, 3.27 mmol) and lithium chloride (0.143 g, 3.39 mmol). The mixture is heated under an argon atmosphere at 120° C. for 1 h and then partitioned between water and CH2C2. The organic layer is washed twice with water (20 mL), dried over magnesium sulfate and concentrated. Column chromatography (50 g silica gel) using ethyl acetate/hexane (20/80) as eluent gave 0.2876 g (78%) of 8-chloro-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol.

Workup

  1. custompartitioned between water and CH2C2
  2. washThe organic layer is washed twice with water (20 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-255d674711e24592809b4fc1722a8ba7
Source dataset
uspto-grants-2002_09
Patent number
US06448397B1

Reaction notes

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