2-Acetylnaphthalene → HCID 73848367, compound

HRID 1737203Notes

Reaction equation

HRID 1737203 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1)(=O)[CH3:2].Cl.[NH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]([O:27][CH3:28])=[O:26]>N1C=CC=CC=1>[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[C:1](=[N:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH3:2]

Participants

4

Reactant 2

HCID 71222-AcetylnaphthaleneHCID 21841974HCID 21841974, compound

Product 1

HCID 73848367HCID 73848367, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

2'-acetonaphthone (1.02 g) and the title compound of Step C (1.39 g) were dissolved in 40 mL of pyridine. The solution was heated to 90° C. for 3 h, and then was cooled to room temperature overnight. The pyridine was removed in vacuo and the residue was taken up in 40 mL of 1N HCl solution and extracted with ethyl acetate (3×50 mL) The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to yield 2.2 g (about 100% yield) of the title compound of Step D as an amber oil. 1H NMR (CDCl3): δ 7.99 (d,1H), 7.86 (m,4H), 7.48 (m,3H), 7.31 (m,3H), 5.33 (s,2H), 3.85 (s,2H), 3.68 (s,3H), 2.34 (s,3H).

Workup

  1. temperaturewas cooled to room temperature overnight
  2. customThe pyridine was removed in vacuo
  3. extractionextracted with ethyl acetate (3×50 mL) The combined organic layers
  4. dry with materialwere dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-daa2ed66aace4d0fa3720ed98ea85fc3
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

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