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 585434Notes

Reaction equation

HRID 585434 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.C1(C)C=CC=CC=1.O>ClCCl>[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 2

HCID 121486191-phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-oneHCID 22272177Toluene water

Product 1

HCID 121486261-Phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-olYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Water is decanted from wet Raney nickel (2.5 g) and toluene is added and additional water is azeotroped off under vacuum. Toluene and decalin (4 mL) are added to the damp Raney nickel and toluene is again azeotroped off. 1-Phenyl-1,2,9,10-tetrahydro[1,4]oxazino[2,3,4-jk]carbazol-7(8H)-one (0.180 g, 0.593 mmol) is added and the mixture is heated at 180° C. (additional toluene/water azeotroping occurs). After 3 h, the mixture is cooled. Dichloromethane is added and the Raney nickel is removed by filtration. The filtrate is concentrated under vacuum until solids begin precipitating out. Hexane is added and the mixture is stored in the refrigerator overnight. The solids are then collected by filtration (wash with hexane) and chromatographed on silica gel gel (30 mL) using ethyl acetate/hexane (20/80) to give 0.119 g (66%) of 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-ol.

Workup

  1. customWater is decanted from wet Raney nickel (2.5 g) and toluene
  2. additionis added
  3. customadditional water is azeotroped off under vacuum
  4. additionToluene and decalin (4 mL) are added to the damp Raney nickel and toluene
  5. customis again azeotroped off
  6. temperaturethe mixture is cooled
  7. customthe Raney nickel is removed by filtration
  8. concentrationThe filtrate is concentrated under vacuum until solids
  9. custombegin precipitating out
  10. additionHexane is added
  11. customis stored in the refrigerator overnight
  12. filtrationThe solids are then collected by filtration (wash with hexane)
  13. customchromatographed on silica gel gel (30 mL)

Sources & evidence

ORD record
ord-91d4f262692d4c72bd1de732373d6be0
Source dataset
uspto-grants-2005_08
Patent number
US06932961B1

Reaction notes

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