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

HRID 1279692Notes

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

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 CH2C2 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

temperatureAfter cooling
customthe mixture is partitioned between CH2C2 and water
dry with materialThe organic layers are dried over sodium sulftate
concentrationconcentrated
customchromatographed on silica gel gel

Sources & evidence

ORD record: ord-a11c7b2e5ca04ce895016e702b6f6264
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448397B1

Reaction notes

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