Sulfuric Acid → 5,6,7-Trichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one

HRID 877490Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:10]N=C2CCCCC2=O)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].OS(O)(=O)=O.[C:24]([O-:27])([O-])=O.[Na+].[Na+]>CC#N>[Cl:9][C:6]1[C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=[C:4]2[C:5]=1[C:2]1[CH2:7][CH2:6][CH2:5][C:24](=[O:27])[C:3]=1[NH:10]2

Participants

Conditions

Temperature: 80 °C

Procedure

2-(2-(3,4,5-Trichlorophenyl)hydrazono)cyclohexanone (1 g, 3.2 mmol) was dissolved in MeCN (10 mL) and aqueous H2SO4 (0.5 mL, 1.8M solution) was added. The reaction mixture was heated to 80° C. for 6 h, basified with saturated Na2CO3 and extracted with EtOAc (2×100 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude material which was purified by silica gel column chromatography [EtOAc-hexane (1:9) as eluant] to give the title compound (0.15 g, 16%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 12.3 (bs, 1H), 7.58 (s, 1H), 3.24 (t, J=12.0 Hz, 2H), 2.59 (t, J=13.0 Hz, 2H), 2.19 (m, 2H).

Workup

extractionextracted with EtOAc (2×100 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated under reduced pressure
customto give the crude material which
customwas purified by silica gel column chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record: ord-6ab8d70a86f846638bcb4015fc1b3cf1
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987319B2

Reaction notes

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