1-Naphthol → HCID 69081849, compound

HRID 2206269Notes

Reaction equation

HRID 2206269 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:19][C:20]1[C:27]([O:28][CH3:29])=[CH:26][C:23]([CH:24]=O)=[CH:22][C:21]=1[Br:30])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:31](#[N:35])[CH2:32][C:33]#[N:34].N1CCCCC1>C(O)C.O>[NH2:35][C:31]1[O:11][C:1]2[C:2]([CH:24]([C:23]3[CH:26]=[C:27]([O:28][CH3:29])[C:20]([O:19][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[C:21]([Br:30])[CH:22]=3)[C:32]=1[C:33]#[N:34])=[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 6746644-(benzyloxy)-3-bromo-5-methoxybenzaldehyde

Product 1

HCID 69081849HCID 69081849, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1-Naphthol (2.16 g, 15 mmol), 4-benzyloxy-3-bromo-5-methoxy-benzaldehyde (4 g, 12.5 mmol) and malononitrile (825 mg, 12.5 mmol) were taken in 30 ml ethanol at room temperature, charged with piperidine (200 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 60 ml water and stirred for about 2 h at room temperature. Thus formed precipitates were collected by filtration, washed with 1:1 mixture of ethanol/water and dried under high vacuum yielding pure solids of the title compound (6.0 g, 11.7 mmol, 93.5%).

Workup

  1. temperatureThe reaction mixture was then cooled down to room temperature
  2. stirringstirred for about 2 h at room temperature
  3. customThus formed
  4. customprecipitates
  5. filtrationwere collected by filtration
  6. washwashed with 1:1 mixture of ethanol/water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-3b989c77d78844309fd63965787e5c60
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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