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

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

Reactant 2

HCID 312751,4-Dioxane

HCID 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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05360800

Reaction notes

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