1,4-Dioxane → 3,4,5,6-Tetrahydro-6-methylazepino[4,3-b]indol-1(2H)-one

HRID 2379137Notes

Reaction equation

HRID 2379137 reaction equation
[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[N:15]O)[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[O:17]1CCOCC1>>[CH3:1][N:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[C:9]2[C:10](=[O:17])[NH:15][CH2:11][CH2:12][CH2:13][C:14]1=2

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 701900HCID 701900, compound

Product 1

HCID 156163063,4,5,6-Tetrahydro-6-methylazepino[4,3-b]indol-1(2H)-one

Procedure

1,2,3,9-Tetrahydro-9-methyl-4H-carbazol-4-one oxime (24 g) and polyphosphoric acid (600 g) in dioxan (500 ml) were treated according to the method described for Intermediate 6. The solid (22 g) obtained by evaporation of the organic extracts was recrystallised from ethyl acetate (300 ml) to give a solid (19.2 g). This was purified by FCC eluting with System A (200:8:1) to give the title compound (5.5 g), m.p. 212°-215°.

Sources & evidence

ORD record
ord-5ec85e6ff1664347895a7534ff569cb2
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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