3-(Dimethylamino)phenol → HCID 9923791, compound

HRID 1786523Notes

Reaction equation

HRID 1786523 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[CH:11]1[C:16]([CH:17]=O)=[CH:15][C:14]2[O:19][CH2:20][O:21][C:13]=2[CH:12]=1.[C:22](#[N:26])[CH2:23][C:24]#[N:25].N1CCCCC1>C(O)C>[NH2:26][C:22]1[O:9][C:5]2[C:6]([CH:17]([C:16]3[CH:11]=[CH:12][C:13]4[O:21][CH2:20][O:19][C:14]=4[CH:15]=3)[C:23]=1[C:24]#[N:25])=[CH:7][CH:8]=[C:3]([N:2]([CH3:10])[CH3:1])[CH:4]=2

Participants

6

Reactant 4

HCID 74213-(Dimethylamino)phenolHCID 8010MalononitrileHCID 8082PiperidineHCID 8438Piperonal

Product 1

HCID 9923791HCID 9923791, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-dimethylaminophenol (489 mg, 3.56 mmol), piperonal (535 mg, 3.56 mmol), and malononitrile (233 mg, 3.53 mmol) in ethanol (20 ml) was added piperidine (0.70 ml, 7.1 mmol). The mixture was stirred at room temperature for 2 h and the resulting solid was collected by filtration, washed with methanol and dried in vacuo to yield the title compound as a yellow solid (940 mg, 2.80 mmol, 79%). 1H NMR (DMSO-d6): 6.83-6.77 (m, 4H), 6.66-6.64 (m, 2H), 6.47-6.44 (m, 1H), 6.21 (s, 1H), 5.96 (s, 1H), 5.95 (s, 1H), 4.53 (s, 1H), 2.85 (s, 6H).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with methanol
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e1920ef2f02749dd94be0827329a4137
Source dataset
uspto-grants-2009_03
Patent number
US07507762B2

Reaction notes

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