Malononitrile → HCID 22136803, compound

HRID 1768417Notes

Reaction equation

HRID 1768417 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[C:16](#[N:20])[CH2:17][C:18]#[N:19].N1CCCCC1>C(O)C>[C:18]([C:17]1[C:16](=[NH:20])[O:1][C:2]2[C:3]([C:4]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2)#[N:19]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8082PiperidineHCID 83482'-Hydroxybenzophenone

Product 1

HCID 22136803HCID 22136803, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
2.5 °C

Procedure

To a mixture of 2-hydroxybenzophenone (2.0 g, 10 mmol) and malononitrile (661 mg, 10 mmol) in ethanol (15 mL) was added piperidine (0.5 mL, 5.0 mmol). The mixture was stirred under 0-5° C. for 2 h. The solvent was evaporated and the residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant, yielding 1.2 g (48%) of the title compound. 1H NMR (CDCl3): 7.74-7.29 (m, 7H), 7.20-7.13 (m, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant

Sources & evidence

ORD record
ord-d5b0e0e88c5640cbb3de89d2383a919e
Source dataset
uspto-grants-2007_06
Patent number
US07235674B2

Reaction notes

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