Water → 9-isobutyl-6-nitro-2,3,4,9-tetrahydro-1H-carbazole

HRID 2272576Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]2=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH:25]([CH3:27])[CH3:26].O>CN(C=O)C>[CH2:24]([N:13]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]2[C:14]1=[CH:15][CH:16]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:25]([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 6-nitro-2,3,4,9-tetrahydro-1H-carbazole (250 mg, 1.16 mmol) and potassium carbonate (479 mg, 3.47 mmol) in DMF (8 mL) was added 1-bromo-2-methylpropane (0.314 mL, 2.89 mmol), and the mixture was stirred at 70° C. for 14 hr. The reaction mixture was cooled, and to the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 55% ethyl acetate/hexane) to give 9-isobutyl-6-nitro-2,3,4,9-tetrahydro-1H-carbazole (296 mg, 1.087 mmol, 94%) as a yellow powder.

Workup

temperatureThe reaction mixture was cooled
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
customdried
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 55% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-854c5d7c02f14ab69167323ba6abcad9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120776B2

Reaction notes

Loading…