1,3-Cyclohexanedione → Benzonitrile, 2-((3-oxo-1-cyclohexen-1-yl)amino)-

HRID 6220

Reaction equation

HRID 6220 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]1(=O)[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH2:11]1>O.O.CC1C=CC(S(O)(=O)=O)=CC=1>[O:16]=[C:12]1[CH2:13][CH2:14][CH2:15][C:10]([NH:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:11]1

Participants

5

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 729132-Aminobenzonitrile

Product 1

HCID 184360Benzonitrile, 2-((3-oxo-1-cyclohexen-1-yl)amino)-Yield 93%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-aminobenzonitrile (120 g) and 1,3-cyclohexandione (120 g) in water (400 ml) was heated to 40° and 4-methylbenzenesulfonic acid monohydrate (6.2 g) was added, with stirring. The mixture was stirred at 40° for 1 hr. The mixture was filtered, and the filter cake was washed with water to provide 200 g (93%) of 2-(3-oxocyclohexen-1-yl)aminobenzonitrile, mp 191.4°.

Workup

  1. temperaturewas heated to 40°
  2. stirringThe mixture was stirred at 40° for 1 hr
  3. filtrationThe mixture was filtered
  4. washthe filter cake was washed with water

Sources & evidence

ORD record
ord-695590d38ba04361a966067c6963981f
Source dataset
uspto-grants-1993_09
Patent number
US05247091

Linked notes

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