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

HRID 2415806Notes

Reaction equation

HRID 2415806 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-47b83a0a23a54ef0adc62c3355300ed8
Source dataset
uspto-grants-2004_11
Patent number
US06821970B2

Reaction notes

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