Malononitrile → HCID 69093549, compound

HRID 2206284Notes

Reaction equation

HRID 2206284 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[CH:17]=O.[C:26](#[N:30])[CH2:27][C:28]#[N:29].C1N2CCN(CC2)C1>C(O)C>[NH2:30][C:26]1[O:12][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH2:1])[N:3]=3)[CH:8]=[CH:7][C:6]=2[CH:17]([C:16]2[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:14]([Br:13])[CH:15]=2)[C:27]=1[C:28]#[N:29]

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 9237DabcoHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 46537882-Amino-8-quinolinol

Product 1

HCID 69093549HCID 69093549, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

2-Amino-8-hydroxyquinoline (192 mg, 1.2 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (245 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) were suspended in 25 ml ethanol at room temperature, charged with DABCO (33 μl, 0.3 mmol) and then stirred at 90° C. under LC-MS control for 6 days. The desired product was formed as a main component with some side products and a small amount of starting material was left. The reaction mixture was cooled down to room temperature, diluted with water to about 100 ml and stirred for over night at room temperature. Thus resulting precipitates were collected by filtration, washed well with 1:1 mixture of ethanol/water and finally with small portion of 10% ethyl acetate in cyclohexane and then dried under high vacuum to get pure solids (202 mg, 0.45 mmol, 45%) of the title compound.

Sources & evidence

ORD record
ord-3f30ecb7cba346be8f2466d3bada9c2e
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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