1-phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-one → 1-Phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol

HRID 585435Notes

Reaction equation

HRID 585435 reaction equation
[C:1]1([CH:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:16](=[O:23])[CH2:17][CH2:18][CH2:19][C:20]=53)=[CH:13][CH:12]=[CH:11][C:10]=4[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OCCOCCO)C.[Pd]>[C:1]1([CH:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:20]3=[CH:19][CH:18]=[CH:17][C:16]=5[OH:23])=[CH:13][CH:12]=[CH:11][C:10]=4[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 121486191-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 47.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8146Diethylene Glycol Monoethyl EtherSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of 1-phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-one (0.0586 g, 0.193 mmol) and 10% Pd/C (0.058 g) in 2-(ethoxyethoxy)ethanol (1 mL) is heated at 190-200° C. for 4 h and then cooled and partitioned between dichloromethane and water. The organic layers are dried over magnesium sulfate, filtered, and the filtrate is concentrated and the residue chromatographed on silica gel using ethyl acetate/hexane (20/80) to give 0.0274 g of 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol.

Workup

  1. temperaturecooled
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic layers are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated
  6. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-b13e0b63291b4c9687b8e32c177c19bb
Source dataset
uspto-grants-2005_08
Patent number
US06932961B1

Reaction notes

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