1-Naphthaldehyde → HCID 135482176, compound

HRID 1862359Notes

Reaction equation

HRID 1862359 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[C:9]1([CH:19]=O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.[NH2:21][C:22]1[CH:26]=[CH:25][NH:24][N:23]=1>C(O)C>[C:9]1([CH:19]2[C:2]3[C:1](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=3[NH:21][C:22]3=[CH:26][CH:25]=[N:24][N:23]23)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 61951-NaphthaldehydeHCID 104341,3-CyclohexanedioneHCID 178418806HCID 178418806, compound

Product 1

HCID 135482176HCID 135482176, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,3-cyclohexanedione (0.11 g, 1 mmol), 1-naphthaldehyde (0.16 g, 1 mmol), and 3-aminopyrazole (0.11 g, 1.27 mmol) in ethanol (10 mL) were heated at 80° C. in a sealed 20 mL vial for 3 days. After the reaction mixture was allowed to cool to ambient temperature, the solvent was evaporated at reduced pressure and the resulting residue was chromatographed on silica gel, eluting with 5% ethanol/methylene chloride to provide 0.14 g (44%) of the title compound.

Workup

  1. customthe solvent was evaporated at reduced pressure
  2. customthe resulting residue was chromatographed on silica gel
  3. washeluting with 5% ethanol/methylene chloride

Sources & evidence

ORD record
ord-00fcf70a13d4438ba0b171157f7feea6
Source dataset
uspto-grants-2003_03
Patent number
US06538000B1

Reaction notes

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