Lithium Chloride → 1-Phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol

HRID 585433Notes

Reaction equation

HRID 585433 reaction equation
Cl[CH:2]1[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.[Li+].[Cl-]>CN(C=O)C>[C:19]1([CH:18]2[N:6]3[C:7]4[C:12]([C:13]5[C:5]3=[CH:4][CH:3]=[CH:2][C:14]=5[OH:15])=[CH:11][CH:10]=[CH:9][C:8]=4[O:16][CH2:17]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 433294Lithium ChlorideHCID 223363418-chloro-1-phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-one

Product 1

HCID 121486261-Phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-olYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 8-chloro-1-phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-one (0.235 g, 0.697 mmol), anhydrous LiCl (0.0355 g, 0.837 mmol), Li2CO3 (0.0618 g, 0.837 mmol), and DMF (1.8 mL) is stirred at 140° C. for 3.5 h. After cooling, the mixture is partitioned between CH2Cl2 and water. The organic layers are dried over sodium sulftate, concentrated, and chromatographed on silica gel gel using EtOAc/hexane (10/90) to give 0.143 g (68%) of 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between CH2Cl2 and water
  3. dry with materialThe organic layers are dried over sodium sulftate
  4. concentrationconcentrated
  5. customchromatographed on silica gel gel

Sources & evidence

ORD record
ord-d561adec5a4e4ec1bd4574d4b1b660bd
Source dataset
uspto-grants-2005_08
Patent number
US06932961B1

Reaction notes

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