2-Acetylnaphthalene → HCID 610454, compound

HRID 1195187Notes

Reaction equation

HRID 1195187 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:3])[CH3:2].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[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](=[O:3])[CH:2]=[CH:16][N:17]([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 71222-AcetylnaphthaleneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 610454HCID 610454, compoundYield 76%

Procedure

2'-Acetonaphthone (10 0 g, 58 mmol, [93-08-3]) was dissolved in 20 mL of N,N-dimethylformamide dimethylacetal [4637-24-5] and the mixture was heated under reflux for 14 hours. The mixture was then cooled, concentrated, and the crystalline residue was recrystallized from cyclohexane to give the title product as orange crystals (9.88 g, 76%). mp 100° -101° . Calc'd for C15H15NO: C 79.97%, H 6.71 %, N 6.22%; found: C 79.71%, H 6.76%, N 6.51%. NMR (CDCl3): 8.40 (s, 1 H); 8.00-7.83 (m, 5 H); 7.54-7.51 (m, 2 H); 5.86 (d, 1 H); 3.33-2.83 (br d, 6 H). Mass spec 226 (M +H+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated
  5. customthe crystalline residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-269cee742e4844d8867209befc9c6b3d
Source dataset
uspto-grants-1992_05
Patent number
US05110831

Reaction notes

Loading…