Malononitrile → HCID 14168963, compound

HRID 1826970Notes

Reaction equation

HRID 1826970 reaction equation
[C:1]([C:3]1[C:4](=[NH:19])[O:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].OC1C=CC=CC=1C(C1C=CC=CC=1)=O.C(#N)CC#N.N1CCCCC1>C(O)C>[NH2:19][C:4]1[O:5][C:6]2[C:11]([CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:3]=1[C:1]#[N:2])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 83482'-HydroxybenzophenoneHCID 22136803HCID 22136803, compound

Product 1

HCID 14168963HCID 14168963, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Cyano-2-imino-4-phenyl-2H-chromene. 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 (8%) 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-3aa49d07eed94ae795f11e7df75e0f07
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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