Malononitrile → HCID 9815099, compound

HRID 1826975Notes

Reaction equation

HRID 1826975 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[C:11](#[N:15])[CH2:12][C:13]#[N:14].N1CCCCC1.[NH2:22][C:23]1[C:28]([NH2:29])=[CH:27][CH:26]=[CH:25][C:24]=1[OH:30]>C(O)C.O>[C:13]([C:12]1[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=2)[C:25]2[C:24](=[C:23]([NH2:22])[C:28]([NH2:29])=[CH:27][CH:26]=2)[O:30][C:11]=1[NH2:15])#[N:14]

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 115693-MethoxybenzaldehydeHCID 5799372,3-Diaminophenol

Product 1

HCID 9815099HCID 9815099, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of m-anisaldehyde (544 mg, 4.0 mmol) and malononitrile (264 mg, 4.0 mmol) in ethanol (10 mL) was added piperidine (0.4 mL) and 2,3-diaminophenol (496 mg, 4.0 mmol). The mixture was stirred at room temperature under argon for 2 h, then it was diluted with water (20 mL). The precipitate was filtered to yield 1.08 g (88%) of the title compound as a brown solid. 1H NMR (CD3OD): 8.02 (s, 1H), 7.05 (t, J=7.8 Hz, 1H), 6.58–6.66 (m, 3H), 6.30 (d, J=7.8 Hz, 1H), 6.08 (d, J=7.8 Hz, 1H), 4.41 (s, 1H), 3.60 (s, 3H).

Workup

  1. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-f4bcab2bfc2c4b30a9f415464558fa9d
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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