Ethanol → HCID 69096596, compound

HRID 2206297Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4](O)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Br:13][C:14]1[C:15]([O:24][CH3:25])=[C:16]([O:22][CH3:23])[CH:17]=[C:18]([CH:21]=1)[CH:19]=O.[C:26](#[N:30])[CH2:27][C:28]#[N:29].C1N2CCN(CC2)C1.C([OH:41])C>O>[NH2:29][C:28]1[O:41][C:3]2[C:2]([NH2:1])=[CH:11][C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[C:4]=2[CH:19]([C:18]2[CH:17]=[C:16]([O:22][CH3:23])[C:15]([O:24][CH3:25])=[C:14]([Br:13])[CH:21]=2)[C:27]=1[C:26]#[N:30]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Aminonaphthol (700.5 mg, 4.4 mmol), 5-bromo-3,4-dimethoxy-benzaldehyde (1.077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 μL, 1.46 mmol) and then stirred at 80° C. under LC-MS control for 24 h. The reaction mixture was cooled down to room temperature, diluted with water to about 100 ml and the precipitates were collected by filtration, washed well with 50% aqueous ethanol and dried under vacuum to yield the title compound (1.55 g, 3.43 mmol, 78%).

Workup

temperatureThe reaction mixture was cooled down to room temperature
filtrationthe precipitates were collected by filtration
washwashed well with 50% aqueous ethanol
customdried under vacuum

Sources & evidence

ORD record: ord-b0e6020a9ea348d0b0fcf063e79b7520
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371333B2

Reaction notes

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