Malononitrile → HCID 9922236, compound

HRID 1826978Notes

Reaction equation

HRID 1826978 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:7]([C:13]#[N:14])[C:8](=[NH:12])[O:9]2)=[CH:4][C:3]=1[Cl:21].CC1C(Cl)=CC(C(C2C=CC=CC=2)=O)=C(O)C=1.C(#N)CC#N.N1CCCCC1>C(O)C>[NH2:12][C:8]1[O:9][C:10]2[C:5]([CH:6]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:7]=1[C:13]#[N:14])=[CH:4][C:3]([Cl:21])=[C:2]([CH3:1])[CH:11]=2

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 5558145-Chloro-2-hydroxy-4-methylbenzophenoneHCID 22136793HCID 22136793, compound

Product 1

HCID 9922236HCID 9922236, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Methyl-6-chloro-3-cyano-2-imino-4-phenyl-2H-chromene. To a mixture of 4-methyl-5-chloro-2-hydroxybenzophenone (500 mg, 2 mmol) and malononitrile (132 mg, 2 mmol) in ethanol (15 mL) was added piperidine (0.1 mL, 1.0 mmol). The mixture was refluxed for 2 h. The solvent was evaporated and the residue was purified by column chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant, yielding 100 mg (17%) of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant

Sources & evidence

ORD record
ord-11d3745a5f174ac6b0bfe4bc3dd2568d
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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