1-Naphthol → HCID 69085069, compound

HRID 2206271Notes

Reaction equation

HRID 2206271 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]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])#[N:28].N1CCCCC1>C(O)C.O>[CH2:33]([O:32][C:30]([C:29]1[CH:20]([C:19]2[CH:22]=[C:23]([O:24][CH3:25])[C:16]([O:15][CH2:12][CH:13]=[CH2:14])=[C:17]([Br:26])[CH:18]=2)[C:2]2[C:1](=[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=2)[O:11][C:27]=1[NH2:28])=[O:31])[CH3:34]

Participants

7

Reactant 4

HCID 70051-NaphtholHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 21681633-Bromo-5-methoxy-4-(2-propen-1-yloxy)benzaldehyde

Product 1

HCID 69085069HCID 69085069, compound

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 ethyl cyanoacetate (113 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 10 ml water, stirred for 2 h at room temperature, solids were collected by filtration, washed with 1:1 mixture of ethanol/water and dried (270 mg, 0.58 mmol, 58%).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringstirred for 2 h at room temperature
  3. filtrationsolids were collected by filtration
  4. washwashed with 1:1 mixture of ethanol/water
  5. customdried (270 mg, 0.58 mmol, 58%)

Sources & evidence

ORD record
ord-ca3a1c900be847a3a3f7c1a66f5fcb10
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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