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

HRID 50616Notes

Reaction equation

HRID 50616 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].[OH-].[K+].[CH:19](I)([CH3:21])[CH3:20].O>CC(C)=O>[CH:19]([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)([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 14797Potassium HydroxideHCID 2587476-nitro-2,3,4,9-tetrahydro-1H-carbazole

Product 1

HCID 22736139N-isopropyl-6-nitro-1,2,3,4-tetrahydrocarbazoleYield 43.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

6-Nitro-1,2,3,4-tetrahydrocarbazole (5.04 g) prepared by the method described in Journal of Chemical Society, p.833 (1924) was dissolved in 50 mL of acetone, and the solution was added with 2.25 g of potassium hydroxide and 8.45 g of isopropyl iodide, warmed to 50° C., and stirred for 3 hours. Water was added to the reaction mixture, and the deposited precipitates were collected to obtain 2.60 g of N-isopropyl-6-nitro-1,2,3,4-tetrahydrocarbazole.

Workup

  1. customthe deposited precipitates
  2. customwere collected

Sources & evidence

ORD record
ord-310fd1766b4945f4a8e7fd852853b56d
Source dataset
uspto-grants-2004_03
Patent number
US06713473B1

Reaction notes

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