1-Naphthol → HCID 69292048, compound

HRID 2206274Notes

Reaction equation

[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[CH:16]=O.[C:23](#[N:27])[CH2:24][C:25]#[N:26].N1CCCCC1>C(O)C.O>[NH2:27][C:23]1[O:11][C:1]2[C:2]([CH:16]([C:15]3[CH:14]=[C:13]([F:12])[C:20]([F:21])=[C:19]([F:22])[CH:18]=3)[C:24]=1[C:25]#[N:26])=[CH:3][CH:4]=[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=21

Participants

Conditions

Temperature: 80 °C

Procedure

1-Naphthol (170 mg, 1.2 mmol), 3,4,5-trifluorobenzaldehyde (160 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) were taken in 7 ml ethanol at room temperature, charged with piperidine (50 μl) and then stirred at 80° C. under LC-MS control till the reaction was complete. The reaction mixture was cooled down to room temperature, diluted with water to about 15 ml and stirred for about 1 h room temperature. The solids were collected by filtration, washed with 60% aq. ethanol and dried under high vacuum to yield the title compound (284 mg, 0.81 mmol, 81%).

Workup

temperatureThe reaction mixture was cooled down to room temperature
stirringstirred for about 1 h room temperature
filtrationThe solids were collected by filtration
washwashed with 60% aq. ethanol
customdried under high vacuum

Sources & evidence

ORD record: ord-3bf63e9a5a294b7aa63b0bcc5336c4eb
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371333B2

Reaction notes

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