1-Naphthol → HCID 5086151, compound

HRID 2206270Notes

Reaction equation

HRID 2206270 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.[CH2:12]([O:15][C:16]1[C:23]([O:24][CH3:25])=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[Br:26])[CH:13]=[CH2:14].[C:27](#[N:31])[CH2:28][C:29]#[N:30].N1CCCCC1>C(O)C.O>[NH2:31][C:27]1[O:11][C:1]2[C:2]([CH:20]([C:19]3[CH:22]=[C:23]([O:24][CH3:25])[C:16]([O:15][CH2:12][CH:13]=[CH2:14])=[C:17]([Br:26])[CH:18]=3)[C:28]=1[C:29]#[N:30])=[CH:3][CH:4]=[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=21

Participants

7

Reactant 4

HCID 70051-NaphtholHCID 8010MalononitrileHCID 8082PiperidineHCID 21681633-Bromo-5-methoxy-4-(2-propen-1-yloxy)benzaldehyde

Product 1

HCID 5086151HCID 5086151, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1-Naphthol (170 mg, 1.2 mmol), 4-allyloxy-3-bromo-5-methoxy-benzaldehyde (271 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 then cooled down to room temperature, diluted with 10 ml water, stirred for 2 h at room temperature, solids were collected by filtration, washed well with 1:1 mixture of ethanol/water and dried under high vacuum yielding 370 mg (0.8 mmol, 80%) of the title compound.

Workup

  1. temperatureThe reaction mixture was then cooled down to room temperature
  2. stirringstirred for 2 h at room temperature
  3. filtrationsolids were collected by filtration
  4. washwashed well with 1:1 mixture of ethanol/water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-6188465caf634546b2904cb62a875135
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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