3-Aminobenzonitrile → HCID 16718203, compound

HRID 2242804Notes

Reaction equation

HRID 2242804 reaction equation
[N+:1](=[C:3]1[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][C:4]1=[O:10])=[N-].[C:11]([C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)N)#[N:12]>C1C=CC=CC=1.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[OH:10][C:4]1[CH2:5][CH2:6][CH2:7][C:8](=[O:9])[C:3]=1[N:1]([C:3]1[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][C:4]=1[OH:10])[C:18]1[CH:19]=[C:13]([CH:14]=[CH:15][CH:17]=1)[C:11]#[N:12]

Participants

5

Reactant 2

HCID 167023-AminobenzonitrileHCID 110624492-diazocyclohexane-1,3-dione

Product 1

HCID 16718203HCID 16718203, compound

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

2-Diazo-cyclohexane-1,3-dione (2 mmoL), prepared by the literature known procedure, 3-cyano-aniline (1 mmoL) and rhodium acetate dimmer (0.01 mmoL) in benzene (10 mL) were heated at 80° C. for 4˜6 hrs. The solid was filtered off and the filtrate was concentrated to give a yellow oil, which was purified by silica gel chromatography to afford the title compound as a white solid.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customto give a yellow oil, which
  4. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-be903b5feff04be99aabd9fca3a4c640
Source dataset
uspto-grants-2010_03
Patent number
US07674793B2

Reaction notes

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