N-isopropyl-6-nitro-1,2,3,4-tetrahydrocarbazole → N-isopropyl-6-amino-1,2,3,4-tetrahydrocarbazole

HRID 50617Notes

Reaction equation

[CH:1]([N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]([N+:17]([O-])=O)[CH:9]=2)([CH3:3])[CH3:2]>C(O)(=O)C.[Fe]>[CH:1]([N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[C:8]([NH2:17])[CH:9]=2)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

The N-isopropyl-6-nitro-1,2,3,4-tetrahydrocarbazole (2.60 g) was dissolved in 100 mL of acetic acid, and the solution was added with 2.75 g of iron powder, warmed to 50° C. and stirred for 3 hours. The reaction mixture was filtered, and the filtrate was diluted by addition of water. The reaction mixture was made basic with 1 N sodium hydroxide solution, and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluent: dichloromethane/ethyl acetate=7/3) to obtain 1.35 g of N-isopropyl-6-amino-1,2,3,4-tetrahydrocarbazole.

Workup

filtrationThe reaction mixture was filtered
additionthe filtrate was diluted by addition of water
extractionextracted with dichloromethane
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography (eluent: dichloromethane/ethyl acetate=7/3)

Sources & evidence

ORD record: ord-0ded96a3980044cdb1aca297937c21d0
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713473B1

Reaction notes

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